Hydrochloric Acid → HCID 178457457, compound

HRID 2169203Notes

Reaction equation

HRID 2169203 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:38]([CH3:40])[CH3:39])[C:12]([C:14]1[NH:15][C:16]([CH2:29][C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:37])=[N:17][C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13])(C(C)(C)C)(C)C.Cl>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH:38]([CH3:40])[CH3:39])[C:12]([C:14]1[NH:15][C:16]([CH2:29][C:30]2[C:31]([Cl:37])=[CH:32][CH:33]=[CH:34][C:35]=2[Cl:36])=[N:17][C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178457491HCID 178457491, compound

Product 1

HCID 178457457HCID 178457457, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Benzyloxy-2-(2,6-dichlorobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (63) (0.17 g, 281 μmol, Eq: 1.00) was dissolved in tetrahydrofuran (1 ml). HCl (211 μl, 422 μmol, Eq: 1.5) was added and the resulting mixture was stirred at room temperature for 30 minutes. The solvent was mostly removed. The residue was partitioned between ethyl acetate and 1M NaOH. The aqueous layer was washed with ethyl acetate, the organic layers were washed with brine, combined, dried over Na2SO4, filtered and concentrated. The remaining oil was triturated and concentrated several times with ether/hexanes to afford 5-benzyloxy-2-(2,6-dichlorobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (64) (0.113 g, 230 μmol, 82.0% yield) as a white solid.

Workup

  1. customThe solvent was mostly removed
  2. customThe residue was partitioned between ethyl acetate and 1M NaOH
  3. washThe aqueous layer was washed with ethyl acetate
  4. washthe organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe remaining oil was triturated
  9. concentrationconcentrated several times with ether/hexanes

Sources & evidence

ORD record
ord-d9ca9b17f70a46d6922112edf7d4aef6
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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