Hydrochloric Acid → HCID 178484637, compound

HRID 2169385Notes

Reaction equation

HRID 2169385 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH3:45])[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[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][CH:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl.CO>O1CCCC1.ClCCl>[OH:8][CH2:9][CH2:10][N:11]([CH3:45])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][CH:36]=3)[CH2:31][CH2:32][CH2:33][CH2:34]2)[N:15]=1)=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178484768HCID 178484768, compound

Product 1

HCID 178484637HCID 178484637, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (350) (280 mg, 0.45 mmol) in tetrahydrofuran (30.0 mL) was added 1N HCl (6.0 mL) at room temperature and the reaction mixture was stirred for 1 h at the same temperature (silica TLC, 5% methanol in dichloromethane, Rf=0.5). The tetrahydrofuran was removed under vacuum and the residue was diluted with water and extracted with ethyl acetate (2×25 mL). The organic layer was washed with NaHCO3 solution (10 mL), water (20 mL) and brine (20 mL). The organic layer was dried and concentrated in vacuum to get a crude mass which was purified by CombiFlash using gradient eluent of ethyl acetate and hexane mixture to get pure 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-methyl-amide (351) (145 mg, 63%) as a white solid.

Workup

  1. customThe tetrahydrofuran was removed under vacuum
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. washThe organic layer was washed with NaHCO3 solution (10 mL), water (20 mL) and brine (20 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuum
  7. customto get a crude mass which
  8. customwas purified by CombiFlash

Sources & evidence

ORD record
ord-3694a8e296574a9fbf43c49aa222c27f
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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