1-Butyl-6-ethoxycarbonyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4,5,8-hexahydro-pyrido(2,3-d)pyrimidine → 1-Butyl-6-ethoxycarbonyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidine

HRID 1461346Notes

Reaction equation

HRID 1461346 reaction equation
[CH2:1]([N:5]1[C:10]2[NH:11][C:12]([CH:27]([CH3:29])[CH3:28])=[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:9]=2[C:8](=[O:30])[NH:7][C:6]1=[O:31])[CH2:2][CH2:3][CH3:4]>ClCCl>[CH2:1]([N:5]1[C:10]2[N:11]=[C:12]([CH:27]([CH3:29])[CH3:28])[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:9]=2[C:8](=[O:30])[NH:7][C:6]1=[O:31])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 198796891-Butyl-6-ethoxycarbonyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4,5,8-hexahydro-pyrido(2,3-d)pyrimidine

Product 1

HCID 198796871-Butyl-6-ethoxycarbonyl-5-(4-fluorophenyl)-7-isopropyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrido(2,3-d)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.35 g (50 mmol) of 2,3-dichloro-4,5-dicyanobenzoquinone are added to a mixture of 21.5 g (50 mmol) of the compound from Example 2 in 800 ml of dichloromethane and the mixture is stirred at room temperature for 1 h. The solution is filtered from a beige precipitate, the filtrate is washed four times with water, the organic phase is dried over sodium sulphate, filtered through a thin layer of active carbon and the filtrate is concentrated in vacuo. The residue is crystallized from ether/petroleum ether.

Workup

  1. filtrationThe solution is filtered from a beige precipitate
  2. washthe filtrate is washed four times with water
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. filtrationfiltered through a thin layer of active carbon
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe residue is crystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-210687ed018c4e8b87b271cf79eb6654
Source dataset
uspto-grants-1991_12
Patent number
US05075311

Reaction notes

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