Hydrochloric Acid → tert-Butyl 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate

HRID 1626781Notes

Reaction equation

HRID 1626781 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[N:11][C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([CH2:35][O:36][Si](C(C)(C)C)(C)C)=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH2:1]([O:8][C:9]1[C:10]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[N:11][C:12]([CH2:16][CH:17]2[CH2:18][CH2:19][N:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([CH2:35][OH:36])=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)[CH2:21][CH2:22]2)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68193315tert-Butyl 5-(benzyloxy)-2-{(1-[4'-({[tert-butyl(dimethyl)silyl]oxy}methyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate

Product 1

HCID 68193244tert-Butyl 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl 5-(benzyloxy)-2-{(1-[4′-({[tert-butyl(dimethyl)silyl]oxy}methyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate (0.98 g, 1.4 mmol) was dissolved in 1,4-dioxane (10 mL), and a solution of hydrogen chloride in dioxane (4 M, 1.0 mL, 4 mmol) was added, followed by stirring at room temperature for 1.5 hours. A saturated sodium hydrogencarbonate solution was added to the reaction solution for neutralization, followed by extraction with ethyl acetate, and subsequently the organic layer was concentrated under reduced pressure to afford the title compound (0.81 g, 1.4 mmol) as a yellow oil (yield 99%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. concentrationsubsequently the organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d9c32070289e4683ad37308659597031
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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