Benzyl Bromide → HCID 58641489, compound

HRID 28379Notes

Reaction equation

HRID 28379 reaction equation
[C:1]([O:4][CH2:5][C:6]1([CH2:23][Cl:24])[C:11]2=[N:12][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:14]([OH:17])[C:15](=[O:16])[N:10]2[CH2:9][CH2:8][O:7]1)(=[O:3])[CH3:2].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>>[C:1]([O:4][CH2:5][C:6]1([CH2:23][Cl:24])[C:11]2=[N:12][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:14]([O:17][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:15](=[O:16])[N:10]2[CH2:9][CH2:8][O:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58641471Ethyl 9-(acetoxymethyl)-9-(chloromethyl)-3-hydroxy-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate

Product 1

HCID 58641489HCID 58641489, compound

Procedure

A solution of ethyl 9-(acetoxymethyl)-9-(chloromethyl)-3-hydroxy-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate (2.05 g, 5.68 mmol) in dimethylfomamide (60 mL) was treated with benzyl bromide (1.46 g, 8.5 mmol, Aldrich) and K2CO3 (1.26 g, 9.1 mmol) and stirred for 16 hrs. Solvent was removed in-vacuo and the crude material was dissolved in ethyl acetate (30 mL) and washed with water (30 mL) and brine (30 mL). The organic solution was dried (Na2SO4), filtered, and concentrated to give an amber oil. This was purified by flash column chromatography, eluting with 5% Et2O in CH2Cl2. Product fractions were pooled and concentrated in-vacuo to give the title compound as a colorless oil: 1H NMR (500 MHz, CDCl3) δ ppm 7.45 (2H, d, J=7.32 Hz), 7.29-7.39 (3H, m), 4.68 (1H, d, J=1 1.90 Hz), 4.37 (1H, d, J=1 1.90 Hz), 4.31 (2H, q, J=7.22 Hz), 4.16-4.24 (2H, m), 4.09-4.16 (1H, m), 4.06 (1H, d, J=11.29 Hz), 3.95-4.03 (1H, m), 3.89 (1H, d, J=1 1.29 Hz), 2.06 (3H, s), 1.56 (2H, s), 1.29 (3H, t, J=7.17 Hz); 13C NMR (126 MHz, CDCl3) δ ppm 170.16, 164.04, 158.67, 150.65, 141.94, 141.67, 136.51, 128.59 128.52, 128.45, 79.57, 74.51, 65.90, 62.11, 60.59, 49.08, 42.16, 20.83, 14.16; HRMS (ESI) calcd for C21H24N2O7Cl (M+H) 451.1272; found 451.1274.

Workup

  1. customSolvent was removed in-vacuo
  2. dissolutionthe crude material was dissolved in ethyl acetate (30 mL)
  3. washwashed with water (30 mL) and brine (30 mL)
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an amber oil
  8. customThis was purified by flash column chromatography
  9. washeluting with 5% Et2O in CH2Cl2
  10. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-efd108f2f5e246e295ab7c8ddd4e06ef
Source dataset
uspto-grants-2008_09
Patent number
US07419969B2

Reaction notes

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