Hydrochloric Acid → HCID 178519974, compound

HRID 2169481Notes

Reaction equation

HRID 2169481 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:41]1[CH2:43][CH2:42]1)[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:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl>O1CCCC1>[CH:41]1([N:11]([CH2:10][CH2:9][OH:8])[C:12]([C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]3([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:15]=2)=[O:13])[CH2:43][CH2:42]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178455281HCID 178455281, compound

Product 1

HCID 178519974HCID 178519974, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropyl-amide (450) (120 mg, 0.199 mmol) of in tetrahydrofuran (6 mL), was added 1N aqueous HCl (1.5 mL) and stirring was continued for 1 h at room temperature. After completion of the reaction, volatiles were removed and the residue was diluted with water (10 mL) and the pH was adjusted to pH 8 by using NaHCO3 and the mixture extracted with ethyl acetate (2×30 mL). The combined extracts were dried and concentrated. The resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography using 50-60% ethyl acetate in hexane as gradient polarity mobile phase to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylicacidcyclopropyl-(2-hydroxyethyl)-amide (451) (80 mg, 82%) as a colorless gummy liquid.

Workup

  1. customAfter completion of the reaction, volatiles
  2. customwere removed
  3. additionthe residue was diluted with water (10 mL)
  4. extractionthe mixture extracted with ethyl acetate (2×30 mL)
  5. customThe combined extracts were dried
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by normal silica gel (100-200 mesh) column chromatography

Sources & evidence

ORD record
ord-1488f9299c104baaa19122d442f4650e
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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