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molecular formula C5H4N4S B1684380 6-Mercaptopurine CAS No. 50-44-2

6-Mercaptopurine

Cat. No. B1684380
M. Wt: 152.18 g/mol
InChI Key: GLVAUDGFNGKCSF-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US06069132

Procedure details

The hypoxanthine analog from Example 3 is reacted with POCl3 at reflux temperature for 50 min to form 7-chloro-1H-1,3-azaphospholo[4,5-d]pyrimidine (compound 14). Reaction of compound 14 with thiourea in boiling ethanol produced the 6-thiopurine analog 1,3-azaphospholo[4,5-d]pyrimidin-7(1H, 6H)-thione (compound 15). Compounds 14 and 15 are prepared as follows:
Name
compound 14
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Two

Identifiers

REACTION_CXSMILES
Cl[C:2]1[C:3]2[NH:10][CH:9]=PC=2[N:5]=[CH:6][N:7]=1.[NH2:11][C:12](N)=[S:13]>C(O)C>[CH:6]1[NH:7][C:2]2[C:12]([N:11]=[CH:9][NH:10][C:3]=2[N:5]=1)=[S:13]

Inputs

Step One
Name
compound 14
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC=1C2=C(N=CN1)P=CN2
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
NC(=S)N
Step Two
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)O

Conditions

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

Outcomes

Product
Name
Type
product
Smiles
C1=NC2=C(N1)C(=S)N=CN2

Source

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.
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