4-Aminobenzyl alcohol → HCID 57474687, compound

HRID 2427997Notes

Reaction equation

HRID 2427997 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-31c4865a930642efb795183ee08a0b26
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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