Diisopropylethylamine → Ethyl {2-methyl-4-[(propyl{4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)methyl]phenoxy}acetate

HRID 1269631Notes

Reaction equation

HRID 1269631 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][NH:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(N(CC)C(C)C)(C)C.CS([C:33]1[N:38]=[C:37]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=2)[CH:36]=[CH:35][N:34]=1)(=O)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][N:16]([CH2:17][CH2:18][CH3:19])[C:33]2[N:38]=[C:37]([C:39]3[CH:40]=[CH:41][C:42]([C:45]([F:48])([F:46])[F:47])=[CH:43][CH:44]=3)[CH:36]=[CH:35][N:34]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 184483542-(Methylsulfonyl)-4-[4-(trifluoromethyl)phenyl]pyrimidineHCID 58622861Ethyl {2-methyl-4-[(propylamino)methyl]phenoxy}acetate

Product 1

HCID 58622894Ethyl {2-methyl-4-[(propyl{4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)methyl]phenoxy}acetateYield 17.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of ethyl {2-methyl-4-[(propylamino)methyl]phenoxy}acetate (652 mg, 2.46 mmol) and N,N-diisopropylethylamine (570 μL, 3.28 mmol) was added 2-(methylsulfonyl)-4-[4-(trifluoromethyl)phenyl]pyrimidine (495 mg, 1.64 mmol) and the resultant mixture heated at 100° C. for 16 h in a reactivial. The cooled reaction mixture was diluted with CH2Cl2 (30 mL), washed with water (20 mL), the aqueous extracted with CH2Cl2 (30 mL) and the CH2Cl2 extracts combined and the solvent removed in vacuo. Purification by Biotage™ chromatography (silica, 90 g) eluted with cyclohexane:EtOAc 10:1 afforded the title compound as a colourless gum (139 mg).

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water (20 mL)
  3. extractionthe aqueous extracted with CH2Cl2 (30 mL)
  4. customthe solvent removed in vacuo
  5. customPurification by Biotage™ chromatography (silica, 90 g)
  6. washeluted with cyclohexane:EtOAc 10:1

Sources & evidence

ORD record
ord-058f92e9dbd046b084f39d0f0e9e1b85
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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