Diisopropylethylamine → 2-Chloro-4-[[[1,1-dimethylethoxy]carbonylmethyl]amino]-5-pyrimidinecarboxylic acid, methyl ester

HRID 1871986Notes

Reaction equation

HRID 1871986 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][N:3]=1.[C:13]([O:17][C:18](=[O:21])[CH2:19][NH2:20])([CH3:16])([CH3:15])[CH3:14].C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:20][CH2:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:21])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 151417Glycine tert-butyl esterHCID 23156323Methyl 2,4-dichloropyrimidine-5-carboxylate

Product 1

HCID 867556542-Chloro-4-[[[1,1-dimethylethoxy]carbonylmethyl]amino]-5-pyrimidinecarboxylic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of step (i) (1.73 g), glycine tert-butyl ester (1.4 g) and N,N-diisopropylethylamine (2.6 ml) in dimethylformamide (20 ml) was stirred at room temperature. After 4 hours, the reaction mixture was partitioned between 2M HCl and ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 5% ethyl acetate in toluene. Yield 1.5 g.

Workup

  1. customthe reaction mixture was partitioned between 2M HCl and ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with 5% ethyl acetate in toluene

Sources & evidence

ORD record
ord-65cb3c76d9f147d2a22a9a1dd8a13932
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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