Hydrochloric Acid → HCID 178484642, compound

HRID 2169218Notes

Reaction equation

HRID 2169218 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH3:42])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl.[OH-].[Na+]>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH3:42])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:15]=1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178484773HCID 178484773, compound

Product 1

HCID 178484642HCID 178484642, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-benzyloxy-2-biphenyl-2-ylmethyl-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (132) (3 g, 4.967 mmol) in tetrahydrofuran (45 mL) was added 1N HCl (7.5 ml, 7.5 mmol) at room temperature and the mixture was stirred for 60 min at room temperature. After completion of the reaction, the mixture was neutralized with 1N sodium hydroxide aqueous solution, extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure to get a crude product which was purified by a normal silica column using 60% ethyl acetate in hexane to get 5-benzyloxy-2-biphenyl-2-ylmethyl-6-hydroxypyrimidine-4-carboxylic acid (2-hydroxyethyl)-methyl-amide (133) (1.7 g, 69.8%) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto get a crude product which
  6. customwas purified by a normal silica column

Sources & evidence

ORD record
ord-88fbdc8adffe47cca04f29f835726957
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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