Methyl 5-amino-2-(3-hydroxyphenyl)-6-(1-(phenylsulfonyl)-1H-indol-4-ylamino)pyrimidine-4-carboxylate → 2-(3-Hydroxyphenyl)-9-(1H-indol-4-YL)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 391697Notes

Reaction equation

HRID 391697 reaction equation
[NH2:1][C:2]1[C:3]([C:34]([NH2:36])=[O:35])=[N:4][C:5]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)=[N:6][C:7]=1[NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2S(C1C=CC=CC=1)(=O)=O.NC1C(C(OC)=O)=NC(C2C=CC=[C:65]([OH:69])C=2)=NC=1NC1C=CC=C2C=1C=CN2S(C1C=CC=CC=1)(=O)=O>N.CO>[OH:33][C:29]1[CH:28]=[C:27]([C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:65](=[O:69])[N:8]3[C:9]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:10]=3[CH:11]=[CH:12][NH:13]4)=[C:3]([C:34]([NH2:36])=[O:35])[N:4]=2)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 57474791Methyl 5-amino-2-(3-hydroxyphenyl)-6-(1-(phenylsulfonyl)-1H-indol-4-ylamino)pyrimidine-4-carboxylateHCID 574747925-Amino-2-(3-hydroxyphenyl)-6-(1-(phenylsulfonyl)-1H-indol-4-ylamino)pyrimidine-4-carboxamide

Product 1

HCID 574747952-(3-Hydroxyphenyl)-9-(1H-indol-4-YL)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

5-Amino-2-(3-hydroxyphenyl)-6-(1-(phenylsulfonyl)-1H-indol-4-ylamino)pyrimidine-4-carboxamide. Methyl 5-amino-2-(3-hydroxyphenyl)-6-(1-(phenylsulfonyl)-1H-indol-4-ylamino)pyrimidine-4-carboxylate (0.1 g, 0.19 mmol) was stirred in 7N NH3/MeOH (20 mL) at 55° C. for 24 h. LCMS shows only the desired product. The mixture was concentrated to afford the title compound, 50 mg, 0.1 mmol, 50%. MS (ESI) m/z 501.5[M+1]+.

Sources & evidence

ORD record
ord-67b131b2dd0b4cbfb51f09b094f7d9c7
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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