Diisopropylethylamine → (S)-methyl 2-(2,6-dichloropyrimidine-4-carboxamido)propanoate

HRID 2276814Notes

Reaction equation

HRID 2276814 reaction equation
Cl.[NH2:2][C@@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5].CCN(C(C)C)C(C)C.[Cl:18][C:19]1[N:24]=[C:23]([C:25](Cl)=[O:26])[CH:22]=[C:21]([Cl:28])[N:20]=1>C(Cl)Cl>[Cl:18][C:19]1[N:24]=[C:23]([C:25]([NH:2][C@@H:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])=[O:26])[CH:22]=[C:21]([Cl:28])[N:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733257Alanine methyl ester hydrochlorideHCID 110311332,6-dichloropyrimidine-4-carbonyl Chloride

Product 1

HCID 89580000(S)-methyl 2-(2,6-dichloropyrimidine-4-carboxamido)propanoateYield 33.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (S)-methyl 2-aminopropanoate hydrochloride (1.397 g, 10.01 mmol) in DCM (80 mL) was added iPr2NEt (4.35 mL, 24.97 mmol). The mixture was stirred for a few minutes and a solution of the 2,6-dichloropyrimidine-4-carbonyl chloride (2.107 g, 9.97 mmol) in DCM (20 mL) was added over a period of 1 minute. After stirring overnight, the reaction was concentrated in vacuo to a residue. The residue was chromatographed over silica gel using 10-40% EtOAc in hexanes. The product fractions were evaporated in vacuo to give (S)-methyl 2-(2,6-dichloropyrimidine-4-carboxamido)propanoate as a yellow oil (0.921 g, 3.31 mmol, 33% yield). LC/MS: m/z=278.1 [M+H]+.

Workup

  1. stirringAfter stirring overnight
  2. concentrationthe reaction was concentrated in vacuo to a residue
  3. customThe residue was chromatographed over silica gel using 10-40% EtOAc in hexanes
  4. customThe product fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-2fbadfe6322e495da162beab7ccf6a46
Source dataset
uspto-grants-2015_09
Patent number
US09133131B2

Reaction notes

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