Methanol → HCID 57751898, compound

HRID 419745Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]4[C:21]5[C:28]([C:29]#[C:30][C:31]([CH3:38])([O:33][Si](C)(C)C)[CH3:32])=[CH:27][NH:26][C:22]=5[N:23]=[CH:24][N:25]=4)[CH2:16][CH2:15]3)[N:11]([CH3:13])[CH:12]=2)=[CH:4][C:3]=1[C:39]([F:42])([F:41])[F:40].C1COCC1.[F-].CO>C(Cl)Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:14]3[CH2:15][CH2:16][N:17]([C:20]4[C:21]5[C:28]([C:29]#[C:30][C:31]([CH3:38])([OH:33])[CH3:32])=[CH:27][NH:26][C:22]=5[N:23]=[CH:24][N:25]=4)[CH2:18][CH2:19]3)[N:11]([CH3:13])[CH:12]=2)=[CH:4][C:3]=1[C:39]([F:40])([F:41])[F:42]

Participants

Conditions

Temperature: 0 °C

Procedure

Charge 4-(4-(4-(4-fluoro-3-(trifluoromethyl)phenyl)-1-methyl-1H-imidazol-2-yl)piperidin-1-yl)-5-(3-methyl-3-(trimethylsilyloxy)but-1-ynyl)-7H-pyrrolo[2,3-d]pyrimidine (0.21 g, 1.0 eq) and THF (2 mL) in a round bottom flask. Cool the reaction mass to 0° C. Add tetra-buytlammonium fluoride (0.19 mL, 2.0 eq) drop wise. Stir the reaction mass at RT for 40 min. Monitor the reaction by TLC (10% MeOH in DCM). Charge ethyl acetate and give washing with saturated sodium bicarbonate solution and saturated aq. sodium chloride. Dry the organic layer over anhy. Na2SO4 and concentrate it under vacuum. Crystallize the product in diethyl ether and filtered it to give 4-(4-(4-(4-(4-fluoro-3-(trifluoromethyl)phenyl)-1-methyl-1H-imidazol-2-yl)piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yn-2-ol (0.11 g, 64%). MS (M+H): m/z=474.6.

Workup

washwashing with saturated sodium bicarbonate solution and saturated aq. sodium chloride
customDry the organic layer over anhy
concentrationNa2SO4 and concentrate it under vacuum
customCrystallize the product in diethyl ether
filtrationfiltered it

Sources & evidence

ORD record: ord-37556018cf7345efb2866ae2ac4e05e0
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093383B2

Reaction notes

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