Hydrochloric Acid → HCID 178457456, compound

HRID 2169209Notes

Reaction equation

HRID 2169209 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:37]([CH3:39])[CH3:38])[C:12]([C:14]1[NH:15][C:16]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Br:36])=[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:37]([CH3:39])[CH3:38])[C:12]([C:14]1[NH:15][C:16]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Br:36])=[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]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178457490HCID 178457490, compound

Product 1

HCID 178457456HCID 178457456, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Benzyloxy-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (69) (0.75 g, 1.22 mmol, Eq: 1.00) was dissolved in tetrahydrofuran (10 ml). HCl (915 μl, 1.83 mmol, Eq: 1.5) was added and the resulting mixture was stirred at room temperature. After 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 brown oil was triturated in ethyl acetate/ether. The solid was collected by filtration, washed with a little ethyl acetate and dried to afford 5-benzyloxy-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (70) (0.21 g, 420 μmol, 34.4% yield) as an off-white solid. The mother liquor also showed clean product (0.43 g, 68% yield) of brown solid.

Workup

  1. customAfter 30 minutes the 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 brown oil was triturated in ethyl acetate/ether
  9. filtrationThe solid was collected by filtration
  10. washwashed with a little ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-d52a6b1f671a47bf8edf7339d822ff56
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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