Ammonium Hydroxide → ethyl 2-aminopyrimidine-5-carboxylate

HRID 1776652Notes

Reaction equation

HRID 1776652 reaction equation
CS([C:5]1[N:10]=[CH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][N:6]=1)(=O)=O.[OH-].[NH4+:17]>C(#N)C>[NH2:17][C:5]1[N:10]=[CH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 254889Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate

Product 1

HCID 295889ethyl 2-aminopyrimidine-5-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (2.15 g, 9.34 mmol) was dissolved in acetonitrile (11.7 ml), and, with stirring at room temperature, aqueous 32% ammonium hydroxide (11.36 ml, 93 mmol) was added drop wise. A white suspension was obtained after few seconds. Acetonitrile was evaporated and the aqueous suspension was filtered on a buckner funnel. The obtained solid was washed with water (20 ml) and dried affording ethyl 2-aminopyrimidine-5-carboxylate as a white solid (1.192 g, 7.13 mmol, 76% yield, MS/ESI+ 168.1 [MH]+).

Workup

  1. customA white suspension was obtained after few seconds
  2. customAcetonitrile was evaporated
  3. filtrationthe aqueous suspension was filtered on a buckner funnel
  4. washThe obtained solid was washed with water (20 ml)
  5. customdried

Sources & evidence

ORD record
ord-63b3e6a65a394312a250e11bcca38dc9
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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