Acetone → (2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)methanol

HRID 59140Notes

Reaction equation

HRID 59140 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([C:22](OCC)=[O:23])[CH:19]=[C:18]([CH2:27][O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[BH4-].[Na+].CC(C)=O>C(O)C.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([CH2:22][OH:23])[CH:19]=[C:18]([CH2:27][O:28][CH2:29][C:30]([F:32])([F:33])[F:31])[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 117823925Ethyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carboxylate

Product 1

HCID 86344246(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of ethyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carboxylate (0.38 g, 0.82 mmol) in ethanol (20 mL), was heated to 45°. Citric acid (1.255 g, 6.53 mmol) and sodium borohydride (0.309 g, 8.16 mmol) were added in portions (of 5-10 mg each) keeping pH within a range of 5-7 over 3 h. Acetone (2 mL) was added and reaction mixture was stirred for 15 min. Chloroform (40 mL) was added. The mixture was filtered and concentrated. The residue was purified by column chromatography on silica column eluting with a gradient of MeOH and DCM to give the title compound as a solid, 0.24 g (69%).

Workup

  1. customreaction mixture
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica column
  5. washeluting with a gradient of MeOH and DCM

Sources & evidence

ORD record
ord-383fb0f12ed047d9b2d4f7cc099681ac
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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