Hydrochloric Acid → HCID 178523453, compound

HRID 2169382Notes

Reaction equation

HRID 2169382 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][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>[OH:8][CH2:9][CH2:10][NH:11][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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178455268HCID 178455268, compound

Product 1

HCID 178523453HCID 178523453, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 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]-amide (346) (290 mg, 0.48 mmol) in tetrahydrofuran (15.0 mL) was added 1N HCl (3.0 mL) at room temperature and the reaction mixture was stirred for 1 h at the same temperature (silica TLC, 5% methanol in dichloromethane/SiO2/UV, Rf=0.5). The tetrahydrofuran was removed in vacuum and the solid obtained was filtered through a sintered funnel, washed with water and ether and dried in vacuum to get pure 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-amide (347) (140 mg, 59%) as a white solid.

Workup

  1. customThe tetrahydrofuran was removed in vacuum
  2. customthe solid obtained
  3. filtrationwas filtered through a sintered funnel
  4. washwashed with water and ether
  5. customdried in vacuum

Sources & evidence

ORD record
ord-d02a9032b2654d17bd0bd31e90c56d51
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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