Ethyl 2-(3-((tert-butyldimethylsilyloxy)methyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate → 2-(3-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 2428014Notes

Reaction equation

HRID 2428014 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]2[N:25]=[C:24]3[C:20]([NH:21][C:22](=[O:34])[N:23]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[C:19]([C:35]([NH2:37])=[O:36])[N:18]=2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.[Si](OCC1C=C(NC2N=C3C(NC(=O)N3C3C=CC=CC=3OC)=C(C(OCC)=O)N=2)C=CC=1)(C(C)(C)C)(C)C>CO.N>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]2[N:25]=[C:24]3[C:20]([NH:21][C:22](=[O:34])[N:23]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[C:19]([C:35]([NH2:37])=[O:36])[N:18]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 57474714Ethyl 2-(3-((tert-butyldimethylsilyloxy)methyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylateHCID 574747152-(3-((tert-Butyldimethylsilyloxy)methyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

Product 1

HCID 574747082-(3-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideYield 91%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

2-(3-((tert-Butyldimethylsilyloxy)methyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide. Ethyl 2-(3-((tert-butyldimethylsilyloxy)methyl)phenyl-amino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate. (0.180 g, 3.97 mmol) was dissolved in methanol (10 mL), saturated with ammonia gas, and reacted according to General Procedure G. After 16 h, the solution was condensed under reduced pressure to afford the title compound (0.153 g, 91%). MS (ESI) m/z 521.6. [M+1]+.

Workup

  1. customreacted
  2. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-3f8fb77f26f043fea9d238e3273bb4f3
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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