HCID 18432862, compound → HCID 15477730, compound

HRID 2305397Notes

Reaction equation

HRID 2305397 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[F:19][C:20]1[CH:27]=[CH:26][C:23]([NH:24][CH3:25])=[CH:22][C:21]=1[C:28]([F:31])([F:30])[F:29]>>[CH3:25][N:24]([C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=2)[CH:5]=[CH:4][N:3]=1)[C:23]1[CH:26]=[CH:27][C:20]([F:19])=[C:21]([C:28]([F:31])([F:29])[F:30])[CH:22]=1

Participants

3

Reactant 2

HCID 18432862HCID 18432862, compoundHCID 18432867HCID 18432867, compound

Product 1

HCID 15477730HCID 15477730, compoundYield 41.5%

Conditions

Temperature
126 °C

Procedure

A round-bottom flask was charged with 1.03 g of 2-chloro-4-(4-fluoro-3-trifluoromethylphenyl)-pyrimidine and 0.82 g of 4-fluoro-3-trifluoromethyl-N-methylaniline and heated to 126° C. for 1.5 h. The reaction mixture melted and subsequently thickened. After standing overnight, the mixture was partitioned between 20 mL of EtOAc and 20 mL of NaHCO3. The organic phase was separated, dried, filtered and evaporated. The crude product was adsorbed onto silica gel and eluted with 50% EtOAc/heptane to yield 0.67 g of an oil which solidified on standing: m.p. 83-84° C.

Workup

  1. customthe mixture was partitioned between 20 mL of EtOAc and 20 mL of NaHCO3
  2. customThe organic phase was separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. washeluted with 50% EtOAc/heptane

Sources & evidence

ORD record
ord-f24d84542a2a4aaf8023502fa1689e04
Source dataset
uspto-grants-2002_08
Patent number
US06440984B1

Reaction notes

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