Triethylamine → HCID 57982687, compound

HRID 1868381Notes

Reaction equation

HRID 1868381 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.[NH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C(N(CC)CC)C>ClCCl>[CH3:16][CH2:8][CH2:6][CH:5]([CH3:12])[CH3:4].[O:20]1[CH2:21][CH2:22][CH:17]([CH2:16][NH:15][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])[CH2:18][CH2:19]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27367082-Chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl chlorideHCID 27732104-Aminomethyltetrahydropyran

Product 2

HCID 78922-MethylpentaneHCID 57982687HCID 57982687, compoundYield 122%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-chloro-4-trifluoromethyl-pyrimidin-5-carbonyl chloride (1.5 g) in dichloromethane (20 ml) at −20 was added a dropwise a solution of 4-aminomethyltetrahydropyran (0.70 g, ex Combi Blocks) and triethylamine (1.05 ml) in dichloromethane (10 ml) and the solution stirred at 0° for 1 hour. Dichloromethane was removed under reduced pressure and ethyl acetate (30 ml) added. The solution was washed with 2N hydrochloric acid (3×20 ml), dried (MgSO4), evaporated and the residue purified using silica gel chromatography with 1:1 ethyl acetate:isohexane to afford 2-chloro-4-trifluoromethyl-pyrimidin-5-carboxylic acid (tetrahydropyran-4-yl-methyl)-amide (1.20 g).

Workup

  1. customDichloromethane was removed under reduced pressure and ethyl acetate (30 ml)
  2. additionadded
  3. washThe solution was washed with 2N hydrochloric acid (3×20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customthe residue purified

Sources & evidence

ORD record
ord-3c51c802bd2744efb92fad9695c7573c
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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