Hydrochloric Acid → 5-(Trifluoromethyl)pyrimidin-2(1H)-one

HRID 247059Notes

Reaction equation

HRID 247059 reaction equation
C(S([C:6]1[N:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1)(=O)=O)C.[OH-:16].[Na+].Cl>>[F:13][C:12]([F:15])([F:14])[C:9]1[CH:8]=[N:7][C:6](=[O:16])[NH:11][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 133170232-Ethylsulfonyl-5-trifluoromethylpyrimidine

Product 1

HCID 133170275-(Trifluoromethyl)pyrimidin-2(1H)-one

Conditions

Temperature
5 °C

Procedure

2-Ethylsulfonyl-5-trifluoromethylpyrimidine (4.7 mmol) was added to 1M NaOH, the mixture stirred at 5° C. for 10 min, then at room temperature for 10 min and finally the pH was adjusted to 2 with HCl. After filtration the filtrate was evaporated, the residue dried and extracted with benzene, the benzene solution evaporated, the residue extracted with boiling ethyl acetate, (3×40 ml), and the ethyl acetate solution evaporated to yield the product; yield 0.50 g (67%). For final purification the product was sublimed at 110°-120° C./0,01 mmHg; m.p. 154° C., 1H NMR (DMSO-d6): δ 8.50 (H-4, H-6), MS [70 eV; m/z (% rel. int.)] 164 (99, M), 145 (21), 136 (100), 117 (25), 116 (16), 109 (11), 90 (28), 89 (40), 75 (35). IR (KBr): 1690 cm-1 (CO).

Workup

  1. waitat room temperature for 10 min
  2. filtrationAfter filtration the filtrate
  3. customwas evaporated
  4. customthe residue dried
  5. extractionextracted with benzene
  6. customthe benzene solution evaporated
  7. extractionthe residue extracted with boiling ethyl acetate, (3×40 ml),
  8. customthe ethyl acetate solution evaporated
  9. customto yield the product
  10. customFor final purification the product
  11. customwas sublimed at 110°-120° C.

Sources & evidence

ORD record
ord-1f4c32fada07464a83fdab150557d7d8
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Reaction notes

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