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

HRID 75958Notes

Reaction equation

HRID 75958 reaction equation
C1(C2NN=C(N[C:10]3[C:15]([F:16])=C[C:13]([CH2:17]N4CCOCC4)=[C:12]([NH:24][C@H:25](C4C=CC(F)=CC=4)C)[N:11]=3)C=2)CC1.[BH4-].[Na+].C[OH:37]>>[F:16][C:15]1[CH:25]=[N:24][C:12]([CH:13]([OH:37])[CH3:17])=[N:11][CH:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 69286265HCID 69286265, compound

Product 1

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

Conditions

Temperature
0 °C

Procedure

1-(5-Fluoropyrimidin-2-yl)ethanone (Method 75, 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-12e1c368cdb64ac493b8f3796e48b192
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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