Ammonium Hydroxide → HCID 86585162, compound

HRID 1280578Notes

Reaction equation

HRID 1280578 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1.[OH-].[NH4+:15]>O1CCCC1.C(N(CC)CC)C>[NH2:15][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[N:3]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 53249641Ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate

Product 1

HCID 86585162HCID 86585162, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A solution of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate (1450 g, 6.23 mole) (Aldrich Chemical Co., Milwaukee, Wis., USA) in 2987 mL of tetrahydrofuran was cooled to 5-10° C. and treated slowly with a mixture of 2407 mL of a 37% solution of ammonium hydroxide in 2978 mL triethylamine. After stirring for 16 hours, the reaction mixture was concentrated in vacuo to approximately 5L and filtered. The filter cake was washed with hexanes and dried in a vacuum oven at 60-65° C. The filtrate was evaporated under reduced pressure to give 1314 g (94%) of ethyl 4-amino-2-methylthiopyrimidine-5-carboxylate as a white solid. m.p. 130.1-130.7° C.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo to approximately 5L
  2. filtrationfiltered
  3. washThe filter cake was washed with hexanes
  4. customdried in a vacuum oven at 60-65° C
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c5890b9d65fa486a8d6e35eee8d49a12
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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