Hydrochloric Acid → HCID 178436098, compound

HRID 2169178Notes

Reaction equation

HRID 2169178 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:29]([N:31]([CH2:40][CH2:41][O:42][Si](C(C)(C)C)(C)C)[CH:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH3:33])=[O:30])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[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>[CH2:1]([O:8][C:9]1[C:10]([C:29]([N:31]([CH2:40][CH2:41][OH:42])[CH:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH3:33])=[O:30])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178436101HCID 178436101, compound

Product 1

HCID 178436098HCID 178436098, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxy-N-(1-phenylethyl)pyrimidine-4-carboxamide (35) (220 mg, 314 μmol, Eq: 1.00) in tetrahydrofuran (5 ml) was added HCl (1N) (471 μl, 471 μmol, Eq: 1.5) at room temperature. The reaction mixture was stirred for 6 hrs, neutralized with 1N NaOH aq. solution, extracted with ethyl acetate, dried (MgSO4), concentrated and chromatographed (silica gel, gradient, 0 to 5% methanol-dichloromethane) to obtain 5-(benzyloxy)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxy-N-(2-hydroxyethyl)-N-(1-phenylethyl)pyrimidine-4-carboxamide (36) (white foam, 161.2 mg, 275 μmol, 87.6% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customchromatographed (silica gel, gradient, 0 to 5% methanol-dichloromethane)

Sources & evidence

ORD record
ord-9d7eee68721e4358b04e46d93ae11304
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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