Triethylamine → 2-Chloro-6-(2,4-difluoro-benzylamino)-pyrimidine-4-carboxylic acid methyl ester

HRID 1497310Notes

Reaction equation

HRID 1497310 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[F:13][C:14]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17].C(N(CC)CC)C>CO>[CH3:11][O:10][C:8]([C:6]1[CH:5]=[C:4]([NH:17][CH2:16][C:15]2[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:14]=2[F:13])[N:3]=[C:2]([Cl:1])[N:7]=1)=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 27332442,4-Difluorobenzylamine

Product 1

HCID 893508542-Chloro-6-(2,4-difluoro-benzylamino)-pyrimidine-4-carboxylic acid methyl esterYield 45.93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of methyl 2,6-dichloropyrimidine-4-carboxylate (1 g, 4.87 mmol) in methanol (20 ml) was cooled to −20° C., to this 2,4-difluoro benzylamine (0.627 mg, 4.39 mmol) and triethylamine (0.98 mg, 9.74 mmol) were added. The reaction mixture 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-b602e19052fb4fdcb5e99bf997cc7a2b
Source dataset
uspto-grants-2015_12
Patent number
US09199962B2

Reaction notes

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