Acetonitrile → HCID 86757426, compound

HRID 1597183Notes

Reaction equation

HRID 1597183 reaction equation
N[C:2]1[C:7]2[N:8]([CH3:13])[C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=[C:4]([F:14])[C:3]=1[N:15]1[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]1=[O:27].[C:28](#N)C.[C:31]([O:35][CH2:36][CH3:37])(=[O:34])[CH:32]=C.C(ON=O)(C)(C)C.[CH2:45]([Cl:47])Cl>O>[Cl:47][CH:45]([CH2:32][C:31]([O:35][CH2:36][CH3:37])=[O:34])[CH2:28][C:2]1[C:7]2[N:8]([CH3:13])[C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=[C:4]([F:14])[C:3]=1[N:15]1[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:24])([F:23])[F:25])[N:17]([CH3:26])[C:16]1=[O:27]

Participants

7

Reactant 5

HCID 6342Acetonitrile2×HCID 6344DichloromethaneHCID 8821Ethyl AcrylateHCID 10906Tert-Butyl nitriteHCID 15538684HCID 15538684, compound

Product 1

HCID 86757426HCID 86757426, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-[5-Amino-7-fluoro-4-methyl-2H-1,4-benzoxazine-3(4H)-on-6-yl]-1-methyl-6-trifluoromethyl-2,4-(1H, 3H)-pyrimidinedione (0.78 g) was mixed with acetonitrile (4 ml), the mixture was slowly added into a flask of −60° C. containing ethyl acrylate (10 ml), acetonitrile (3 ml), CuCl2 (0.35 g) and tert-butylnitrite (0.4 ml). After stirring for 1 hr, the cooling bath was removed and reaction continued for 15 hr. Water (15 ml) and methylene chloride (30 ml) were added and the heavier phase was washed with water (20 ml×3) and then dried over sodium sulfate. After filtration and evaporation, the residue was purified by column chromatography (silica gel, hexane to 25% ethyl acetate) to yield the title compound (0.2 g) as a diastereomeric mixture.

Workup

  1. additionthe mixture was slowly added into a flask of −60° C.
  2. customthe cooling bath was removed
  3. customreaction
  4. waitcontinued for 15 hr
  5. washthe heavier phase was washed with water (20 ml×3)
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration and evaporation
  8. customthe residue was purified by column chromatography (silica gel, hexane to 25% ethyl acetate)

Sources & evidence

ORD record
ord-831424d9f76d4fd8ac9f4d00292326ce
Source dataset
uspto-grants-2001_09
Patent number
US06294503B1

Reaction notes

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