Hydrochloric Acid → HCID 178484642, compound

HRID 2169137Notes

Reaction equation

HRID 2169137 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 53.33%

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 (9-01) (2.1 g, 3.602 mmol) in tetrahydrofuran (30 mL) was added 1N HCl (5.4 ml, 5.4 mmol) at room temperature. 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 using 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 (10-01) (900 mg, 53.33%) as a floppy light yellow 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

Sources & evidence

ORD record
ord-3aba0ff0bdc4440d9f237bfc74b9210c
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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