Water → HCID 54515013, compound

HRID 650630Notes

Reaction equation

HRID 650630 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH3:28])[C:8]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:12][C:13](COS(C)(=O)=O)=[N:14][CH:15]=1)=[O:9].C(Cl)Cl.[OH2:41]>>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH3:28])[C:8]([C:10]1[C:11]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:12][C:13]([CH2:28][N:7]2[CH2:8][CH2:10][O:41][CH2:5][CH2:6]2)=[N:14][CH:15]=1)=[O:9]

Participants

4

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 54354681HCID 54354681, compound

Product 1

HCID 54515013HCID 54515013, compoundYield 88%

Procedure

To a solution of 0.40 g (0.73 mmol) methanesulfonic acid 5-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4-phenyl-pyrimidin-2-ylmethyl ester in 5 ml CH2Cl2 0.095 ml (1.10 mmol) morpholine were added. The reaction mixture was stirred for 16 hrs. at RT. The reaction mixture was 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 10:1) to give 0.33 g (88%) 2-morpholin-4-ylmethyl-4-phenyl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a pale yellow waxy solid, MS (ISP): 539.3 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-2bfc106a14ad41a28a41f15f1eb13876
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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