Methanethiol → 2-Amino-4-fluoromethyl-6-methylthiopyrimidine

HRID 3912

Reaction equation

HRID 3912 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](F)[CH:5]=[C:4]([CH2:9][F:10])[N:3]=1.[CH3:11][SH:12].O1CCCC1.[Na]>CO>[NH2:1][C:2]1[N:3]=[C:4]([CH2:9][F:10])[CH:5]=[C:6]([S:12][CH3:11])[N:7]=1

Participants

6

Reactant 4

HCID 878MethanethiolHCID 8028TetrahydrofuranHCID 5360545SodiumHCID 201534984-Fluoro-6-(fluoromethyl)pyrimidin-2-amine

Product 1

HCID 201534912-Amino-4-fluoromethyl-6-methylthiopyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.0 part of 2-amino-4-fluoro-6-fluoromethylpyrimidine, 3.0 parts of methanethiol and 50 parts of dry tetrahydrofuran was stirred at 5° C. whilst a solution of 0.16 parts of sodium in 20 parts of dry methanol was added dropwise. The temperature was kept below 10° C. with ice-bath cooling. When the addition was complete, stirring was continued for 1 hour. The resulting solution was evaporated and the residue was diluted with water and extracted three times with 50 parts of ether. The ethereal solutions were combined and dried (MgSO4). The solvent was evaporated and the crude product was purified by recrystallisation from carbon tetrachloride to give 2-amino-4-fluoromethyl-6-methylthiopyrimidine m.p. 95°-97° C.

Workup

  1. additionwas added dropwise
  2. customThe temperature was kept below 10° C. with ice-bath
  3. temperaturecooling
  4. additionWhen the addition
  5. customThe resulting solution was evaporated
  6. additionthe residue was diluted with water
  7. extractionextracted three times with 50 parts of ether
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated
  10. customthe crude product was purified by recrystallisation from carbon tetrachloride

Sources & evidence

ORD record
ord-2890b78e01af42029f6cf55bc787a012
Source dataset
uspto-grants-1988_02
Patent number
US04723006

Linked notes

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