Benzyl Bromide → Ethyl 3-(benzyloxy)-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylate

HRID 1365742Notes

Reaction equation

HRID 1365742 reaction equation
[OH:1][C:2]1[C:14](=[O:15])[N:6]2[CH2:7][CH2:8][O:9][CH2:10][C:11]([CH3:13])([CH3:12])[C:5]2=[N:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:21]([O:1][C:2]1[C:14](=[O:15])[N:6]2[CH2:7][CH2:8][O:9][CH2:10][C:11]([CH3:13])([CH3:12])[C:5]2=[N:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58877856Ethyl 3-hydroxy-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylate

Product 1

HCID 58877852Ethyl 3-(benzyloxy)-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Ethyl 3-hydroxy-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylate (790 mg, 2.8 mmol) and benzyl bromide (580 mg, 3.4 mmol) were placed together in 10 mL DMF under N2 and treated with K2CO3 (512 mg, 4 mmol). After warming for 2.5 h at 60-70° C., the DMF was removed under reduced pressure. The residue was dissolved in CH2Cl2 and washed with H2O. The CH2Cl2 solution was dried over MgSO4, filtered and concentrated to give the title compound (940 mg, 90%) as a solid. 1H NMR (300 MHz, CDCl3) δ: 1.27 (t, J=7.3 Hz, 3H), 1.54 (s, 6H), 3.59 (s, 2H), 3.65-3.95 (m, 2H), 4.30 (q, J=7.3 Hz, 2H), 4.40-4.80 (m, 2H), 5.19 (s, 2H), 7.29-7.34 (m, 3H), 7.39-7.49 (m, 2H). LC/MS (M+H): 373.

Workup

  1. customthe DMF was removed under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with H2O
  4. dry with materialThe CH2Cl2 solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-34ee0f05994b4f47b110aba6ef2aced6
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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