Pyridine → HCID 19745816, compound

HRID 2253590Notes

Reaction equation

HRID 2253590 reaction equation
N1C=CC=CC=1.[O:7]=[C:8]1[N:13]([CH2:14][C:15]#[CH:16])[C:12]2[CH:17]=[C:18]([N:21]3[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[NH:23][C:22]3=O)[CH:19]=[CH:20][C:11]=2[O:10][CH2:9]1.P(Cl)(Cl)([Cl:35])=O>C1(C)C=CC=CC=1>[Cl:35][C:22]1[N:21]([C:18]2[CH:19]=[CH:20][C:11]3[O:10][CH2:9][C:8](=[O:7])[N:13]([CH2:14][C:15]#[CH:16])[C:12]=3[CH:17]=2)[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[N:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 19745797HCID 19745797, compound

Product 1

HCID 19745816HCID 19745816, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

16.61 g of pyridine are added at 25° C. while stirring to a suspension of 25.55 g of 3-[3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (see Example 3) and 32.13 g of phosphorus oxychloride in 250 ml of toluene. The reaction mixture is heated to 100° C. for 6 hours, cooled to 25° C. and poured on to 500 g of ice. Subsequently, the aqueous mixture is extracted three times with 150 ml of ethyl acetate each time and the organic phase is washed neutral with water, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The resinous product is purified by chromatography on a silica gel column with ethyl acetate/n-hexane (1:3) as the eluent. Finally, the product is recrystallized from diethyl ether/n-hexane. In this manner there is obtained 6-[2-chloro-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one, m.p. 143°-145° C. (see Example 78).

Workup

  1. temperaturecooled to 25° C.
  2. extractionSubsequently, the aqueous mixture is extracted three times with 150 ml of ethyl acetate each time
  3. washthe organic phase is washed neutral with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to dryness under reduced pressure
  6. customThe resinous product is purified by chromatography on a silica gel column with ethyl acetate/n-hexane (1:3) as the eluent
  7. customFinally, the product is recrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-2661e7f1422445778aad579eda94318c
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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