Dimethylformamide → HCID 23295687, compound

HRID 1953967Notes

Reaction equation

HRID 1953967 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:3]=1.O[C:20]1C=[CH:23][S:22][C:21]=1[C:25]([F:28])([F:27])[F:26].[C:29]([O-:32])([O-])=O.[K+].[K+].CN(C)[CH:37]=[O:38]>>[F:16][C:15]([F:18])([F:17])[C:12]1[CH:13]=[CH:14][C:9]([C:4]2[N:5]=[C:6]([O:38][C:37]3[CH:20]=[C:21]([C:25]([F:28])([F:27])[F:26])[S:22][CH:23]=3)[CH:7]=[C:2]([O:32][C:29]3[CH:20]=[C:21]([C:25]([F:26])([F:27])[F:28])[S:22][CH:23]=3)[N:3]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 15477095HCID 15477095, compoundHCID 23295691HCID 23295691, compound

Product 1

HCID 23295687HCID 23295687, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 4,6-dichloro-2-(α,α,α-trifluoro-p-tolyl)pyrimidine (2.15 g, 7.34 mmol) and 3-hydroxy-2-(trifluoromethyl)thiophene (2.47 g, 14.7 mmol) in dimethylformamide is treated with K2CO3 (2.52 g, 18.3 mmol), heated at 100° C. for 3 hours, cooled to room temperature, poured onto water and neutralized with 6N HCL to pH 6-7. The resultant reaction mixture is extracted with ether. The ether extracts are washed sequentially with water and brine, dried over MgSO4 and concentrated in vacuo to give a yellow solid residue. The residue is purified by flash chromatography (silica gel, methylene chloride) to afford the title product as an off-white solid, 3.03 g (74%), mp 93-95° C. identified by 1HNMR, 13CNMR, mass spectral and elemental analyses.

Workup

  1. temperaturecooled to room temperature
  2. additionpoured onto water and neutralized with 6N HCL to pH 6-7
  3. customThe resultant reaction mixture
  4. extractionis extracted with ether
  5. washThe ether extracts are washed sequentially with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto give a yellow solid residue
  9. customThe residue is purified by flash chromatography (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-33e1df8c88f04e8f852e49024dc36d23
Source dataset
uspto-grants-2000_09
Patent number
US06121202

Reaction notes

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