Tetrahydrofuran → HCID 42642397, compound

HRID 2091535Notes

Reaction equation

HRID 2091535 reaction equation
[CH2:1]([C@:4]1([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:9][CH2:8][N:7]([C@H:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:11])[C:6](=[O:16])[NH:5]1)[CH:2]=[CH2:3].C1C[O:27]CC1>>[CH3:13][C:12]([CH3:14])([CH3:15])[C@@H:10]([N:7]1[CH2:8][CH2:9][C@@:4]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([CH2:1][CH2:2][CH2:3][OH:27])[NH:5][C:6]1=[O:16])[CH3:11]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 58485258HCID 58485258, compound

Product 1

HCID 42642397HCID 42642397, compoundYield 12%

Procedure

To a solution of (R)-4-allyl-1-((S)-3,3-dimethylbutan-2-yl)-4-(4-fluorophenyl)tetrahydropyrimidin-2(1H)-one (100 mg, 0.31 mmol) in THF (3 mL) was added BH3 THF (1 mL, 1 mol/L) at 0° C. under nitrogen atmosphere. The formed mixture was stirred for 2 h. The reaction was quenched with water. Aqueous NaOH solution (3 mol/L, 0.2 mL) and H2O2 (30%, 0.2 mL) were added and the resulting mixture was stirred for 1.5 h. The mixture was extracted with ethyl acetate and the combined organic phase was concentrated to give the crude product, which was purified by preparative TLC to give (R)-1-((S)-3,3-dimethylbutan-2-yl)-4-(4-fluorophenyl)-4-(3-hydroxypropyl)tetrahydropyrimidin-2(1H)-one (12 mg, 12%). 1H NMR (CDCl3): 0.73 (s, 3H), 1.04 (d, 3H), 1.29 (m, 1H), 1.48 (m, 1H), 1.81-2.07 (m, 4H), 2.46 (s, 1H), 2.57 (m, 1H), 3.07 (m, 1H), 3.58 (m, 1H), 4.46 (m, 1H), 5.93 (s, 1H), 6.98-7.03 (m, 2H), 7.29 (m, 2H).

Workup

  1. customThe reaction was quenched with water
  2. additionAqueous NaOH solution (3 mol/L, 0.2 mL) and H2O2 (30%, 0.2 mL) were added
  3. stirringthe resulting mixture was stirred for 1.5 h
  4. extractionThe mixture was extracted with ethyl acetate
  5. concentrationthe combined organic phase was concentrated
  6. customto give the crude product, which
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-1d23c4407dca41ae88f67de4fe87e40e
Source dataset
uspto-grants-2013_05
Patent number
US08440658B2

Reaction notes

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