Ammonium Chloride → 2-(2-(3-Methoxy-4-(2-methyloxazol-5-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidin-4-yl)propan-2-ol

HRID 59174Notes

Reaction equation

HRID 59174 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([C:22](=[O:24])[CH3:23])[CH:19]=[C:18]([CH2:25][O:26][CH2:27][C:28]([F:31])([F:30])[F:29])[N:17]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1.[CH3:32][Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([C:22]([OH:24])([CH3:32])[CH3:23])[CH:19]=[C:18]([CH2:25][O:26][CH2:27][C:28]([F:29])([F:30])[F:31])[N:17]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1178211031-(2-(3-Methoxy-4-(2-methyloxazol-5-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidin-4-yl)ethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 863451622-(2-(3-Methoxy-4-(2-methyloxazol-5-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidin-4-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(2-(3-Methoxy-4-(2-methyloxazol-5-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidin-4-yl)ethanone (64 mg, 0.15 mmol) was dissolved in THF (5 mL) and was added slowly to a solution of methylmagnesium bromide (3 M in THF, 0.391 mL, 1.17 mmol) in THF (5 mL). The mixture was stirred for 5 min. The mixture was cooled on ice bath and ammonium chloride (sat, aq, 5 mL) was added. The mixture was stirred for 5 min. The mixture was extracted with EtOAc (×2). The solvents were evaporated and the residue was purified by column chromatography eluting with a gradient of methanol in DCM to give the title compound as a solid, 46 mg (69%).

Workup

  1. temperatureThe mixture was cooled on ice bath
  2. stirringThe mixture was stirred for 5 min
  3. extractionThe mixture was extracted with EtOAc (×2)
  4. customThe solvents were evaporated
  5. customthe residue was purified by column chromatography
  6. washeluting with a gradient of methanol in DCM

Sources & evidence

ORD record
ord-9906f6f4814c41f89f677eb754ab5836
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

Loading…