Diisopropylethylamine → (S)-tert-butyl 6-((1-amino-1-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxylate

HRID 1752399Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.Cl.[NH2:17][C@@H:18]([CH3:22])[C:19]([NH2:21])=[O:20].CCN(C(C)C)C(C)C>C(#N)C>[NH2:21][C:19](=[O:20])[C@@H:18]([NH:17][C:4]1[N:3]=[C:2]([Cl:1])[N:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]=1)[CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the tert-butyl 2,6-dichloropyrimidine-4-carboxylate (0.626 g, 2.51 mmol) in acetonitrile (10 mL) was added (S)-2-aminopropanamide hydrochloride (0.319 g, 2.56 mmol) and iPr2NEt (0.96 mL, 5.5 mmol). The mixture was heated at 50° C. for 6 h then concentrated in vacuo. The residue was chromatographed over silica gel using 50-100% EtOAc in hexanes. The product fractions were evaporated in vacuo to give (S)-tert-butyl 6-((1-amino-1-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxylate as an off-white foam (0.628 g, 2.09 mmol, 83% yield). LC/MS: m/z=301.2 [M+H]+.

Workup

concentrationthen concentrated in vacuo
customThe residue was chromatographed over silica gel using 50-100% EtOAc in hexanes
customThe product fractions were evaporated in vacuo

Sources & evidence

ORD record: ord-d073e6a2cc844ac18920fabaf2722e22
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163008B2

Reaction notes

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