Ethanolamine → HCID 57474695, compound

HRID 2428007Notes

Reaction equation

HRID 2428007 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-891c381cfdff4a8f9fa396056dc87e09
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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