Sodium Nitrite → 2-methylsulfanyl-6-[3-(trifluoromethyl)phenyl]-1H-pyrimidin-4-one

HRID 2053085Notes

Reaction equation

HRID 2053085 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7](N)[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=1.N([O-])=[O:21].[Na+]>C(O)(=O)C>[CH3:1][S:2][C:3]1[N:8]=[C:7]([OH:21])[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 585132282-Methylsulfanyl-6-(3-trifluoromethylphenyl)-pyrimidin-4-ylamine

Product 1

HCID 1785035332-methylsulfanyl-6-[3-(trifluoromethyl)phenyl]-1H-pyrimidin-4-oneYield 86.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Methylsulfanyl-6-(3-trifluoromethylphenyl)-pyrimidin-4-ylamine (2.42 g) was heated to 40° C. in acetic acid (6 ml) until dissolved. A solution of sodium nitrite (1.17 g in 5 ml water) was added dropwise and stirring continued for 30 minutes at 40° C. and 90 minutes at 90° C. The reaction mixture was allowed to cool to room temperature and filtered. The cake was washed with water then dissolved in ethyl acetate (200 mL) and washed with saturated sodium bicarbonate (2×300 ml). Organics were separated, dried over sodium sulphate and solvent was evaporated under reduced pressure to yield product 2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-ol (2.11 g) as a pale yellow solid.

Workup

  1. dissolutionuntil dissolved
  2. filtrationfiltered
  3. washThe cake was washed with water
  4. dissolutionthen dissolved in ethyl acetate (200 mL)
  5. washwashed with saturated sodium bicarbonate (2×300 ml)
  6. customOrganics were separated
  7. dry with materialdried over sodium sulphate and solvent
  8. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-f605e2ba4d4847bea4611058ad5f47e9
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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