Ammonia → 2-Chloropyrimidine-4-carboxamide

HRID 1752403Notes

Reaction equation

HRID 1752403 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=O)[CH:5]=[C:4](N[C@@H](C)C(OC)=O)[N:3]=1.CO.[NH3:21]>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH2:21])=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 89422478(S)-methyl 2-chloro-6-((1-methoxy-1-oxopropan-2-yl)amino)pyrimidine-4-carboxylate

Product 1

HCID 2470282-Chloropyrimidine-4-carboxamideYield 89%

Procedure

A solution of the (S)-methyl 2-chloro-6-((1-methoxy-1-oxopropan-2-yl)amino)pyrimidine-4-carboxylate (3.719 g, 13.59 mmol) in 7M ammonia in methanol (20 mL, 140 mmol) was heated in a sealed tube for 3 days at 50° C. After cooling, the precipitated solid was filtered off and rinsed with MeOH (2×5 mL) then dried under vacuum at 40° C. to give (S)-6-(1-amino-1-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxamide as a pale yellow powder (2.946 g, 12.09 mmol, 89% yield). LC/MS: m/z=244.2 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated solid was filtered off
  3. washrinsed with MeOH (2×5 mL)
  4. customthen dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-fffaac5e3a0f483a8bc6d2a4e1ec409b
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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