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 391679Notes

Reaction equation

HRID 391679 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-aded75ce782743968b95c943d54f6fbf
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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