2-(4-Trifluoromethyl-phenyl)-pyrimidine-5-carbaldehyde → (+/-)-1-(2-(4-(Trifluoromethyl)phenyl)pyrimidin-5-yl)butan-1-ol

HRID 1427535Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[CH2:19]([Mg]Br)[CH2:20][CH3:21]>C1COCC1>[F:18][C:2]([F:1])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[CH:11][C:12]([CH:15]([OH:16])[CH2:19][CH2:20][CH3:21])=[CH:13][N:14]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a −78° C. solution of 2-(4-(trifluoromethyl)phenyl)pyrimidine-5-carbaldehyde (1.0 g, 3.96 mmol) in THF (20 mL) was added n-propylmagnesium bromide (2.97 mL of a 2.0M solution in THF, 5.95 mmol). The solution was stirred at 0° C. for two hours. The mixture was quenched with saturated aqueous NH4Cl, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography to give (+/−)-1-(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-yl)butan-1-ol (1.1 g) as a red oil. 1H NMR (400 MHz, CDCl3) δ 8.75 (s, 2H), 8.50 (d, J=8.0 Hz, 2H), 7.68 (d, J=8.0 Hz, 2H), 4.79-4.68 (m, 1H), 1.98-1.91 (m, 1H), 1.85-1.63 (m, 2H), 1.47-1.29 (m, 2H), 0.92 (t, J=7.2 Hz, 3H).

Workup

customThe mixture was quenched with saturated aqueous NH4Cl
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-5200245a78434ebf8d2591352e3f1984
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933104B2

Reaction notes

Loading…