Hydrochloric Acid → HCID 178457444, compound

HRID 2169469Notes

Reaction equation

HRID 2169469 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:41]([CH3:43])[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([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.C([O-])(O)=O.[Na+]>O1CCCC1.O>[OH:8][CH2:9][CH2:10][N:11]([CH:41]([CH3:43])[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([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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178457480HCID 178457480, compound

Product 1

HCID 178457444HCID 178457444, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylicacid[2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (438) (150 mg, 0.248 mmol) of in tetrahydrofuran (4 mL), was added 1N HCl (1 mL), then this reaction mixture was stirred for 1 h, at room temperature, After completion of the reaction, volatile substances were removed the from the reaction, then dilute with water (10 mL) and adjust with NaHCO3 to pH8, then extract with ethyl acetate (2×30 mL), then organic part was dried over sodium sulfate, then concentrated, 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-carboxylicacid (2-hydroxyethyl)-isopropylamide (439) (100 mg, 82%) as white sticky liquid.

Workup

  1. customAfter completion of the reaction, volatile substances
  2. customwere removed the
  3. customfrom the reaction
  4. extractionextract with ethyl acetate (2×30 mL)
  5. dry with materialorganic part was dried over sodium sulfate
  6. concentrationconcentrated
  7. customresulting crude product
  8. customwas purified by normal silica gel (100-200 mesh) column chromatography

Sources & evidence

ORD record
ord-25b39e5760cd4da0a617b303410cce39
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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