Ammonia → (S)-6-((3-amino-2-hydroxy-3-oxopropyl)amino)-2-chloropyrimidine-4-carboxamide

HRID 1752413Notes

Reaction equation

HRID 1752413 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([Cl:10])[N:7]=[C:6]([NH:11][CH2:12][C@H:13]([OH:18])[C:14](OC)=[O:15])[CH:5]=1)(=[O:3])[NH2:2].[NH3:19].CO>>[NH2:19][C:14](=[O:15])[C@@H:13]([OH:18])[CH2:12][NH:11][C:6]1[N:7]=[C:8]([Cl:10])[N:9]=[C:4]([C:1]([NH2:2])=[O:3])[CH:5]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 89422638(S)-methyl 3-((6-carbamoyl-2-chloropyrimidin-4-yl)amino)-2-hydroxypropanoate

Product 1

HCID 89422640(S)-6-((3-amino-2-hydroxy-3-oxopropyl)amino)-2-chloropyrimidine-4-carboxamideYield 94%

Conditions

Temperature
50 °C

Procedure

A mixture of the (S)-methyl 3-((6-carbamoyl-2-chloropyrimidin-4-yl)amino)-2-hydroxypropanoate (0.421 g, 1.53 mmol) and 7M ammonia in MeOH (10 mL, 70 mmol) were heated in a sealed tube at 50° C. overnight. The precipitated solid was filtered off from the warm reaction mixture, rinsed once with 5 mL MeOH, and air-dried to give (S)-6-((3-amino-2-hydroxy-3-oxopropyl)amino)-2-chloropyrimidine-4-carboxamide as a light tan powder (0.372 g, 1.43 mmol, 94% yield). LC/MS: m/z=260.1 [M+H]+.

Workup

  1. filtrationThe precipitated solid was filtered off from the warm reaction mixture
  2. washrinsed once with 5 mL MeOH
  3. customair-dried

Sources & evidence

ORD record
ord-018dbf5b100a4c048e725cd4f4897080
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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