4-Aminobenzyl alcohol → HCID 57474687, compound

HRID 391662Notes

Reaction equation

HRID 391662 reaction equation
OC[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([C:16](OCC)=[O:17])[C:13]([N+:21]([O-])=O)=[C:12]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])[N:11]=2)=[CH:5][CH:4]=1.Cl[C:34]1N=C(C(OCC)=O)C([N+]([O-])=O)=[C:36]([NH:48][C:49]2[CH:54]=CC=CC=2OC)[N:35]=1.NC1C=CC([CH2:62][OH:63])=CC=1.C([N:69](C(C)C)CC)(C)C>CN(C)C=O>[N:35]1([CH2:34][C:3]2[CH:4]=[CH:5][C:6]([NH:9][C:10]3[N:11]=[C:12]4[C:13]([NH:21][C:62](=[O:63])[N:24]4[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[O:31][CH3:32])=[C:14]([C:16]([NH2:69])=[O:17])[N:15]=3)=[CH:7][CH:8]=2)[CH:54]=[CH:49][N:48]=[CH:36]1

Participants

6

Reactant 4

HCID 693314-Aminobenzyl alcoholHCID 81531DiisopropylethylamineHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 57474683HCID 57474683, compound

Product 1

HCID 57474687HCID 57474687, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-(4-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate. Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (See Example 30.A) (0.250 g, 0.710 mmol), 4-aminobenzyl alcohol (0.104 g, 0.852 mmol) and diisopropylethylamine (0.137 g, 1.065 mmol) 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 (60-100% ethyl acetate in hexanes) to afford the title compound (0.374 g, >100%). MS (ESI) m/z 440.0 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-5c8ccc7cf124427e92a9ff34742e07c4
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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