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

HRID 2428019
Notes
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Reaction equation

HRID 2428019 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]1[N:25]=[C:24]2[C:20]([NH:21][C:22](=[O:34])[N:23]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])=[C:19]([C:35]([NH2:37])=[O:36])[N:18]=1)(C(C)(C)C)(C)C.[Si](OCC1C=CC=CC=1NC1N=C2C(NC(=O)N2C2C=CC=CC=2OC)=C(C(OCC)=O)N=1)(C(C)(C)C)(C)C>CO.N>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]1[N:25]=[C:24]2[C:20]([NH:21][C:22](=[O:34])[N:23]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])=[C:19]([C:35]([NH2:37])=[O:36])[N:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 57474722Ethyl 2-(2-((tert-butyldimethylsilyloxy)methyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylateHCID 574747232-(2-((tert-Butyldimethylsilyloxy)methyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

Product 1

HCID 574747162-(2-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideYield 90%

Reagents, catalysts & solvents 2

HCID 222
Ammonia
Solvent
HCID 887MethanolSolvent

Procedure

2-(2-((tert-Butyldimethylsilyloxy)methyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide. Ethyl 2-(2-((tert-butyldimethylsilyloxy)methyl)phenyl-amino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate (0.190 g, 3.97 mmol) was dissolved in methanol (15 mL) and saturated with ammonia gas according to General Procedure G. After 16 h, the solution was condensed under reduced pressure to afford the title compound (0.150 g, 90%). MS (ESI) m/z 521.6. [M+1]+.

Workup

  1. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-5cdea7fdb5e44b08aaee6737d61cfcef
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968556B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes