Dimethyl Sulfide → 2-(4-((2-Cyclopentyl-6-ethylpyrimidin-4-yl)methyl)phenyl)ethanol

HRID 1508934Notes

Reaction equation

HRID 1508934 reaction equation
[CH:1]1([C:6]2[N:11]=[C:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20](O)=[O:21])=[CH:15][CH:14]=3)[CH:9]=[C:8]([CH2:23][CH3:24])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(C)C>C1COCC1.CO>[CH:1]1([C:6]2[N:11]=[C:10]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][OH:21])=[CH:17][CH:18]=3)[CH:9]=[C:8]([CH2:23][CH3:24])[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 1068Dimethyl SulfideHCID 901119292-(4-((2-Cyclopentyl-6-ethylpyrimidin-4-yl)methyl)phenyl)acetic acid

Product 1

HCID 901117502-(4-((2-Cyclopentyl-6-ethylpyrimidin-4-yl)methyl)phenyl)ethanolYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-((2-cyclopentyl-6-ethylpyrimidin-4-yl)methyl)phenyl)acetic acid (0.050 g, 0.15 mmol) in THF (5 mL) at rt under a nitrogen atmosphere was treated with BH3.SMe2 (0.047 g, 0.62 mmol) and the mixture was heated at 55° C. for 4 h. After this time, the mixture was cooled, diluted with methanol, and concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.013 g, 30%) as a yellow oil. MW=310.43. 1H NMR (DMSO-d6, 500 MHz) δ 7.22-7.17 (m, 2H), 7.16-7.11 (m, 2H), 7.00 (s, 1H), 4.58 (t, J=5.2 Hz, 1H), 3.93 (s, 2H), 3.60-3.53 (m, 2H), 3.21 (quin, J=8.1 Hz, 1H), 2.71-2.58 (m, 4H), 2.01-1.91 (m, 2H), 1.88-1.79 (m, 2H), 1.78-1.69 (m, 2H), 1.67-1.57 (m, 2H), 1.16 (t, J=7.6 Hz, 3H); APCI MS m/z 311 [M+H]+.

Workup

  1. temperatureAfter this time, the mixture was cooled
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9b679e8beeb94f92aac79c36078515f3
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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