Synthesis routes of 4-{6-[8-Cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester

4-{6-[8-Cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester

Número de catálogo B8676315

Peso molecular: 575.7 g/mol

Clave InChI: ZSUHBFDUYDVOFZ-UHFFFAOYSA-N

Atención: Solo para uso de investigación. No para uso humano o veterinario.

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Patent

US07863278B2

Procedure details

A suspension of 4-[6-(6-bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (5.93 g, 0.010 mol, prepared as in Example 1), tetrakis(triphenylphosphine)palladium(0) (1.40 g, 0.00121 mol), and tributyl(1-ethoxyvinyl)tin (5.32 mL, 0.0157 mol) in toluene (30 mL) was heated under reflux for 3.5 hours. The mixture was cooled and filtered to give a solid. Purification of the solid by silica gel chromatography using a gradient of 5%-66% ethyl acetate/hexane over 15 minutes gave 4-{6-[8-cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester as a yellow foam (4.50 g, 78%). MS (APCl) M++1: calc'd 576.2, found, 576.3.

Name

4-[6-(6-bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester

Quantity

5.93 g

Type

reactant

Reaction Step One

Name

tributyl(1-ethoxyvinyl)tin

Quantity

5.32 mL

Type

reactant

Reaction Step One

Name

toluene

Quantity

30 mL

Type

solvent

Reaction Step One

Name

tetrakis(triphenylphosphine)palladium(0)

Quantity

1.4 g

Type

catalyst

Reaction Step One

Name

4-{6-[8-cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester

Yield

78%

Identifiers

REACTION_CXSMILES

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[C:30]([CH3:31])=[C:29](Br)[C:28](=[O:33])[N:27]([CH:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[C:25]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:44]([O:46][CH2:47][CH3:48])=[CH2:45])CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[C:30]([CH3:31])=[C:29]([C:44]([O:46][CH2:47][CH3:48])=[CH2:45])[C:28](=[O:33])[N:27]([CH:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[C:25]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2] |^1:67,69,88,107|

Inputs

Step One

Name	4-[6-(6-bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester
Quantity	5.93 g
Type	reactant
Smiles	C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C=NC(=CC1)NC=1N=CC2=C(N1)N(C(C(=C2C)Br)=O)C2CCCC2

Name	tributyl(1-ethoxyvinyl)tin
Quantity	5.32 mL
Type	reactant
Smiles	C(CCC)[Sn](C(=C)OCC)(CCCC)CCCC

Name	toluene
Quantity	30 mL
Type	solvent
Smiles	C1(=CC=CC=C1)C

Name	tetrakis(triphenylphosphine)palladium(0)
Quantity	1.4 g
Type	catalyst
Smiles	C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1

Conditions

Other

Conditions are dynamic	1
Details	See reaction.notes.procedure_details.

Workups

TEMPERATURE

Type	TEMPERATURE
Details	was heated

TEMPERATURE

Type	TEMPERATURE
Details	under reflux for 3.5 hours
Duration	3.5 h

TEMPERATURE

Type	TEMPERATURE
Details	The mixture was cooled

FILTRATION

Type	FILTRATION
Details	filtered

CUSTOM

Type	CUSTOM
Details	to give a solid

CUSTOM

Type	CUSTOM
Details	Purification of the solid by silica gel chromatography

CUSTOM

Type	CUSTOM
Details	over 15 minutes
Duration	15 min

Outcomes

Product

Name	4-{6-[8-cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester
Type	product
Smiles	C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C=NC(=CC1)NC=1N=CC2=C(N1)N(C(C(=C2C)C(=C)OCC)=O)C2CCCC2

Measurements

Type	Value	Analysis
AMOUNT: MASS	4.5 g
YIELD: PERCENTYIELD	78%
YIELD: CALCULATEDPERCENTYIELD	78.2%

Source

Open Reaction Database (ORD)

Description

The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.