2-Aminobenzyl alcohol → HCID 57474716, compound

HRID 391680

Reaction equation

HRID 391680 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 57474573HCID 57474573, compoundHCID 57474717HCID 57474717, compound

Product 1

HCID 57474716HCID 57474716, compoundYield 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-0f74feac840e4890ab527f36cd025e46
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Linked notes

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