Triethylamine → 2-Chloro-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide

HRID 1868378Notes

Reaction equation

HRID 1868378 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12](Cl)=[O:13])=[CH:4][N:3]=1.[CH:15]1([CH2:21][NH2:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C>ClCCl>[CH:15]1([CH2:21][NH:22][C:12]([C:5]2[C:6]([C:8]([F:11])([F:10])[F:9])=[N:7][C:2]([Cl:1])=[N:3][CH:4]=2)=[O:13])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 27367082-Chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl chloride

Product 1

HCID 579825812-Chloro-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-chloro-4-trifluoromethyl-pyrimidin-5-carbonyl chloride (750 mg, ex Maybridge) in dichloromethane (15 ml) at −400 was added dropwise over 30 minutes a solution of cyclohexanemethanamine (0.35 ml, ex Lancaster) and triethylamine (0.41 ml) in dichloromethane (15 ml). Dichloromethane was removed under reduced pressure and ethyl acetate (20 ml) added. The solution was washed sequentially with water, 5% sodium bicarbonate solution and water, dried (MgSO4), evaporated and triturated with ether:hexane to afford 2-chloro-trifluoromethyl-pyrimidine-5-carboxylic acid cyclohexylmethyl-amide (666 mg).

Workup

  1. customDichloromethane was removed under reduced pressure and ethyl acetate (20 ml)
  2. additionadded
  3. washThe solution was washed sequentially with water, 5% sodium bicarbonate solution and water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customtriturated with ether

Sources & evidence

ORD record
ord-f6c130dcb31c45da8f75a93dd22e5c0d
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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