Pivalic acid → HCID 131735128, compound

HRID 929885Notes

Reaction equation

HRID 929885 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[C:14]([F:15])=[C:13]([F:16])[CH:12]=[C:11]([F:17])[C:10]=2[F:18])[CH:5]=[CH:4][N:3]=1.CC(C)(C)C(O)=O>>[F:15][C:14]1[C:13]([F:16])=[CH:12][C:11]([F:17])=[C:10]([F:18])[C:9]=1[O:8][C:6]1[CH:5]=[CH:4][N:3]=[CH:2][N:7]=1

Participants

3

Reactant 2

HCID 6417Pivalic acidHCID 117993165HCID 117993165, compound

Product 1

HCID 131735128HCID 131735128, compound

Conditions

Temperature
60 °C

Procedure

To a mixture of 2-chloro-4-(2,3,5,6-tetrafluorophenoxyl)pyrimidine (compound no. C-2, 200 mg, 0.72 mmol) and 2,2-dimethylpropanoic acid (733 mg, 0.412 mL, 7.2 mmol, 10 eq.) was added the aromatic or heterocyclic amine (1.08 mmol, 1.5 eq.) and the mixture was heated to 60° C. for 2 h. The reaction mixture was partitioned between a mixture of water and diethyl ether. The organic layer was washed with water two times, aqueous 0,1M sodium hydroxide and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to yield light yellow solids which were triturated in a small amount of 50/50 diethyl ether/petroleum ether, filtered and dried to yield 2-(N-aryl/heterocyclyl-N—H/alkyl)-4-(2,3,5,6-tetrafluorophenoxyl)pyrimidine (compound no. 4) as white solids.

Workup

  1. customThe reaction mixture was partitioned between a mixture of water and diethyl ether
  2. washThe organic layer was washed with water two times, aqueous 0,1M sodium hydroxide and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield light yellow solids which
  7. customwere triturated in a small amount of 50/50 diethyl ether/petroleum ether
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-897e93caaffe4eeab4c8eabcc6964e55
Source dataset
uspto-grants-2016_03
Patent number
US09296727B2

Reaction notes

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