Ammonia → HCID 89422611, compound

HRID 1752439Notes

Reaction equation

HRID 1752439 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[C:4]([N:12]2[CH2:16][C@H:15]([OH:17])[C@@H:14]([OH:18])[CH2:13]2)[N:3]=1.[NH3:19]>CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH2:19])=[O:9])[CH:5]=[C:4]([N:12]2[CH2:16][C@H:15]([OH:17])[C@@H:14]([OH:18])[CH2:13]2)[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 89422526HCID 89422526, compound

Product 1

HCID 89422611HCID 89422611, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-chloro-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)pyrimidine-4-carboxylate (1.132 g, 4.14 mmol) in 7M ammonia in MeOH (12 mL) was allowed to sit at ambient temperature overnight. The reaction mixture was evaporated in vacuo and the residue was taken up in EtOAc (10 mL). The residue first dissolved then quickly precipitated a solid. After cooling back down to ambient temperature the precipitated solid was filtered off then dried under vacuum at 40° C. to give 2-chloro-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)pyrimidine-4-carboxamide as a tan powder (0.969 g, 3.75 mmol, 91% yield). LC/MS: m/z=259.2 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionThe residue first dissolved
  3. customthen quickly precipitated a solid
  4. filtrationwas filtered off
  5. customthen dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-cd8905287fa245598bf711fc45252a19
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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