Ethanolamine → HCID 57474695, compound

HRID 391672Notes

Reaction equation

HRID 391672 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]([O:13]CC)=O)[C:8]([N+:16]([O-])=O)=[C:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[N:6]=1.ClC1N=C([C:35](OCC)=[O:36])C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=1.C(C[NH2:55])O.C(N(C(C)C)CC)(C)C>CN(C)C=O>[OH:1][CH2:2][CH2:3][NH:4][C:5]1[N:6]=[C:7]2[C:8]([NH:16][C:35](=[O:36])[N:19]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])=[C:9]([C:11]([NH2:55])=[O:13])[N:10]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 57474573Ethyl 2-chloro-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 86627723HCID 86627723, compound

Product 1

HCID 57474695HCID 57474695, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-(2-hydroxyethylamino)-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), ethanolamine (0.052 g, 0.852 mmol) and diisopropylethylamine (0.137 g, 1.06 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 (0-100% ethyl acetate in hexanes) to afford the title compound (0.250 g, 95%). MS (ESI) m/z 378.5 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-3509174425f241e69ff26abf2a4a002b
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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