Thiourea → 6-Mercaptopurine

HRID 1108777Notes

Reaction equation

HRID 1108777 reaction equation
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]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 178478399HCID 178478399, compound

Product 1

HCID 6674906-Mercaptopurine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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:

Sources & evidence

ORD record
ord-2166634f657847c8a5872e0229336246
Source dataset
uspto-grants-2000_05
Patent number
US06069132

Reaction notes

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