Hydrochloric Acid → HCID 178484640, compound

HRID 2169473Notes

Reaction equation

HRID 2169473 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH3:41])[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>[OH:8][CH2:9][CH2:10][N:11]([CH3:41])[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]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178484771HCID 178484771, compound

Product 1

HCID 178484640HCID 178484640, compound

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]-methyl-amide (442) (180 mg, 0.313 mmol) of in tetrahydrofuran (10 mL), was added 1N HCl (2 mL), then this reaction mixture was stirred for 1 h, at room temperature, After completion of the reaction, volatiles were removed from the reaction mixture and the residue was diluted with water (10 mL) and pH was adjusted with NaHCO3 to 8. The quenched mass was extracted with ethyl acetate (2×50 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 a gradient polarity mobile phase to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-methyl-amide (443).

Workup

  1. customAfter completion of the reaction, volatiles
  2. customwere removed from the reaction mixture
  3. additionthe residue was diluted with water (10 mL) and pH
  4. extractionThe quenched mass was extracted with ethyl acetate (2×50 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-13b1239c159b4417a64f9c12a3c3758c
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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