4-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine → 2-(4-(5-Methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidin-4-yloxy)phenyl)propane-1,3-diol

HRID 1619445Notes

Reaction equation

CC1(C)[O:7][CH2:6][CH:5]([C:8]2[CH:34]=[CH:33][C:11]([O:12][C:13]3[C:18]([CH3:19])=[C:17]([O:20][CH:21]4[CH2:26][CH2:25][N:24]([C:27]5[N:32]=[CH:31][CH:30]=[CH:29][N:28]=5)[CH2:23][CH2:22]4)[N:16]=[CH:15][N:14]=3)=[CH:10][CH:9]=2)[CH2:4][O:3]1>CC(C)=O>[CH3:19][C:18]1[C:13]([O:12][C:11]2[CH:33]=[CH:34][C:8]([CH:5]([CH2:6][OH:7])[CH2:4][OH:3])=[CH:9][CH:10]=2)=[N:14][CH:15]=[N:16][C:17]=1[O:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[N:28]=[CH:29][CH:30]=[CH:31][N:32]=2)[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 27 °C

Procedure

To a solution of 4-(4-(2,2-dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methyl-6-(1-(pyrimidin-2-yl)piperidin-4-yloxy)pyrimidine (1.5 gm, 0.0031 moles) in acetone (20 ml) conc. HCl (2 ml) was added portion-wise and the reaction mixture was stirred for 3 hours at 27° C. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield 700 mg product as white solid

Workup

concentrationThe reaction mixture was concentrated
dissolutionthe residue was dissolved in ethyl acetate
extractionThe organic extract
washwas successively washed with water & brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-985647bc66194a8db781db9ba6cf052c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772302B2

Reaction notes

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