Methanol → 1-(5-Fluoropyrimidin-2-yl)ethan-1-ol

HRID 415420Notes

Reaction equation

HRID 415420 reaction equation
ClC1C(NC2C=C(C)NN=2)=NC(N[C@H:9]([C:11]2[N:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=2)[CH3:10])=NC=1.[BH4-].[Na+].C[OH:28]>>[F:17][C:14]1[CH:13]=[N:12][C:11]([CH:9]([OH:28])[CH3:10])=[N:16][CH:15]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 16659841Azd-1480

Product 1

HCID 665706531-(5-Fluoropyrimidin-2-yl)ethan-1-olYield 99%

Conditions

Temperature
0 °C

Procedure

1-(5-Fluoropyrimidin-2-yl)ethanone (Method 5, 0.77 g) was dissolved in MeOH (15 ml), and the solution was cooled to 0° C. NaBH4 (0.210 g, 5.55 mmol) was added. The mixture was stirred at room temperature for 1 hour and then partitioned between EtOAc and H2O. The organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated to give the title compound as a yellowish oil (0.79 g, 99%). 1H NMR (CDCl3) δ 8.65 (s, 2H), 5.20 (m, 1H), 4.00 (br s, 1H), 1.80 (d, 3H).

Workup

  1. custompartitioned between EtOAc and H2O
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9e35277a6a594f4a83d67d83a55f2ee5
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

Loading…