Hydrochloric Acid → HCID 178457455, compound

HRID 2169199Notes

Reaction equation

HRID 2169199 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:26]([N:28]([CH2:32][CH2:33][O:34][Si](C(C)(C)C)(C)C)[CH:29]([CH3:31])[CH3:30])=[O:27])=[N:11][C:12]([CH2:16][C:17]([CH3:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>O1CCCC1.O>[CH2:1]([O:8][C:9]1[C:10]([C:26]([N:28]([CH2:32][CH2:33][OH:34])[CH:29]([CH3:31])[CH3:30])=[O:27])=[N:11][C:12]([CH2:16][C:17]([CH3:18])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:25])=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178457489HCID 178457489, compound

Product 1

HCID 178457455HCID 178457455, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(Benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-6-hydroxy-N-isopropyl-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxamide (57) (62 mg, 107 μmol, Eq: 1.00) was stirred in tetrahydrofuran (2 ml), HCl (aqueous) (161 μl, 161 μmol, Eq: 1.5) was added. The reaction mixture was stirred at room temperature for 3.0 hours, 160 μl 1N NaOH was added and the reaction mixture was diluted with water, extracted twice with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Trituration in hexanes/ether was conducted to give 5-(benzyloxy)-6-hydroxy-N-(2-hydroxyethyl)-N-isopropyl-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxamide (58) (32 mg, 64%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-1acdde4cdf224d408d757e04a98a4f96
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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