3-Aminobenzyl alcohol → 2-(3-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 2428010Notes

Reaction equation

HRID 2428010 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]=[C:22]([CH2:26][OH:27])[CH:21]=2)=[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=C(C=CC=1)CO.C(N(C(C)C)CC)(C)C>CN(C)C=O>[OH:27][CH2:26][C:22]1[CH:21]=[C:20]([NH:19][C:7]2[N:8]=[C:9]3[C:4]([NH:1][C:40](=[O:41])[N:10]3[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[C:5]([C:28]([NH2:57])=[O:29])[N:6]=2)[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 802933-Aminobenzyl alcoholHCID 81531DiisopropylethylamineHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 57474709Ethyl 5-nitro-2-(3-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

Product 1

HCID 574747082-(3-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-nitro-2-(3-(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), 3-aminobenzyl alcohol (0.125 g, 1.2 mmol) and diisopropylethylamine (0.219 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 (0.350 g., 93%). MS (ESI) m/z 440.5 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-6519bb3c80b04ab998195f882db57efc
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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