Water → HCID 53933798, compound

HRID 354005Notes

Reaction equation

HRID 354005 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][N:7]([CH3:25])[C:8]([C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:14][N:13]=[C:12]([CH2:23]Cl)[N:11]=1)=[O:9].C(Cl)Cl.[OH2:38]>>[F:30][C:29]([F:31])([F:32])[C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([C:2]([F:34])([F:33])[F:1])[CH:28]=1)[CH2:6][N:7]([CH3:25])[C:8]([C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:14][N:13]=[C:12]([CH2:23][N:7]2[CH2:8][CH2:10][O:38][CH2:5][CH2:6]2)[N:11]=1)=[O:9]

Participants

4

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 54223796HCID 54223796, compound

Product 1

HCID 53933798HCID 53933798, compoundYield 62%

Procedure

To a solution of 0.58 g (1.11 mmol) 2-chloromethyl-5-(2-chloro-phenyl)-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide in 10 ml CH2Cl2 0.24 ml (2.78 mmol) morpholine were added. The reaction mixture was stirred for 16 hrs. at RT and than poured into H2O and extracted three times with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 200:10:1) to give 0.40 g (62%) 5-(2-chloro-phenyl)-2-morpholin-4-ylmethyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a colorless foam, MS (ISP): 573.1 (M+H+).

Workup

  1. extractionextracted three times with 50 ml CH2Cl2
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 200:10:1)

Sources & evidence

ORD record
ord-cd6867f8c0964778a95b517a9e20c50b
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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