Hydrochloric Acid → HCID 178457437, compound

HRID 2169295Notes

Reaction equation

HRID 2169295 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:42]([CH3:44])[CH3:43])[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([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH:42]([CH3:44])[CH3:43])[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([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178457474HCID 178457474, compound

Product 1

HCID 178457437HCID 178457437, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (257) (0.7 g, 1.13 mmol) in tetrahydrofuran (10.0 mL) was added HCl (0.062 g, 1.70 mmol) and the reaction mixture was stirred at room temperature for 1.5 h. After completion of the reaction, the mixture was extracted with ethyl acetate. The combined organic layer was washed with water, separated and dried over Na2SO4. After evaporation of the solvent, the crude product was purified by normal silica gel column chromatography (using 60% ethyl acetate in hexane followed by 5% methanol in ethyl acetate) to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (258) (0.43 g, 75.0%) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation of the solvent
  7. customthe crude product was purified by normal silica gel column chromatography (using 60% ethyl acetate in hexane followed by 5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-c09dd0da38c04b5f831538f7a2d99d62
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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