2-Aminobenzyl alcohol → 2-(2-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 2428015Notes

Reaction equation

HRID 2428015 reaction equation
[N+:1]([C:4]1[C:5]([C:28](OCC)=[O:29])=[N:6][C:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][OH:27])=[N:8][C:9]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])([O-])=O.ClC1N=C([C:40](OCC)=[O:41])C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=1.[NH2:57]C1C=CC=CC=1CO.C(N(C(C)C)CC)(C)C>CN(C)C=O>[OH:27][CH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:19][C:7]1[N:8]=[C:9]2[C:4]([NH:1][C:40](=[O:41])[N:10]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[C:5]([C:28]([NH2:57])=[O:29])[N:6]=1

Participants

6

Reactant 4

HCID 214392-Aminobenzyl alcoholHCID 81531DiisopropylethylamineHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 57474717HCID 57474717, compound

Product 1

HCID 574747162-(2-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-nitro-2-(2-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (See Example 30.A) (0.300 g, 0.852 mmol), 2-aminobenzyl alcohol (0.125 g, 1.2 mmol) and diisopropylethylamine (0.296 g) were reacted according to General Procedure C, except at room temperature and in dimethylformamide (5 ml). The crude reaction mixture was condensed and purified using Biotage chromatography (60 to 100% EtOAc in hexanes) to afford the title compound (0.323 g, 86%). MS (ESI) m/z 440.5 [M+1]+.

Workup

  1. customThe crude reaction mixture
  2. customcondensed
  3. custompurified

Sources & evidence

ORD record
ord-2df7bcb29eea4bf9bc488ef051896b76
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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