Methanol → HCID 86730176, compound

HRID 1850140Notes

Reaction equation

HRID 1850140 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13](=[O:15])[CH3:14])[N:8]=2)=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([CH:13]([OH:15])[CH3:14])[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86730177HCID 86730177, compound

Product 1

HCID 86730176HCID 86730176, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-(4-fluorophenoxy)pyrimidin-2-yl)ethanone (0.150 g 0.646 mmol) was taken up in 2.5 mL 4:1 MeOH:DCM, and cooled to 0° C. NaBH4 (49 mg 1.30 mmol) was added. Fizzing was observed. After 10 min, cold bath was removed, and the reaction was stirred 1 h. Solvent was removed in vacuo. White residue was taken up in 10 mL water, and extracted with (2×10 mL) EtOAc. Washed organics with 10 mL brine. Dried over Na2SO4. Filtered and concentrated to give 143 mg (95%) 1-(4-(4-fluorophenoxy)pyrimidin-2-yl)ethanol as a colorless oil. Anal. RP-HPLC tR=1.38 min. (Column=Inertsil C8 Column, 3.0 μm, 3.0×30 mm. Column Temperature=50° C. Eluents=A: Water (5 mM Ammonium formate, 2% ACN); B: ACN. Flow Rate=2 mL/min. Gradient=0 min 5% B; 5% to 95% B in 1.70 min; 0.3 min 95% B; 2.1 min 1% B.) MS m/z 235.1 (M+H)+.

Workup

  1. customcold bath was removed
  2. customSolvent was removed in vacuo
  3. extractionextracted with (2×10 mL) EtOAc
  4. dry with materialDried over Na2SO4
  5. filtrationFiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8f2fffef53b4f3188025a9cd764048c
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

Loading…