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

HRID 391675Notes

Reaction equation

HRID 391675 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-978a5e4b93fe448c954fd25959519667
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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