Triethylamine → (2,6-Dichloro-pyrimidin-4-yl)-(2,4-difluoro-benzyl)-amine

HRID 1497313Notes

Reaction equation

HRID 1497313 reaction equation
C[C:2]1[C:3]([Cl:10])=[N:4][C:5]([Cl:9])=[N:6][C:7]=1Cl.[F:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH2:14][NH2:15].C(N(CC)CC)C>CO>[Cl:9][C:5]1[N:6]=[C:7]([NH:15][CH2:14][C:13]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:12]=2[F:11])[CH:2]=[C:3]([Cl:10])[N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2327892,4,6-Trichloro-5-methylpyrimidineHCID 27332442,4-Difluorobenzylamine

Product 1

HCID 89350889(2,6-Dichloro-pyrimidin-4-yl)-(2,4-difluoro-benzyl)-amineYield 37.97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of methyl 2,4,6-trichloropyrimidine (1 g, 4.87 mmol) in methanol (20 ml) was cooled −20° C., to this 2,4-difluoro benzylamine (0.627 mg, 4.39 mmol) and triethylamine (0.98 mg, 9.74 mmol) were added. RM was stirred at same temperature for 1 hr then at room temperature for 4 hrs. Methanol was removed under vacuum. The residue was purified by column chromatography to get the title compound.

Workup

  1. additionwere added
  2. waitat room temperature for 4 hrs
  3. customMethanol was removed under vacuum
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b9771b4aad3e46d88f91b90e222d3dc3
Source dataset
uspto-grants-2015_12
Patent number
US09199962B2

Reaction notes

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