Potassium Carbonate → Ethyl 3-hydroxy-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylate

HRID 1365741Notes

Reaction equation

HRID 1365741 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][C:6]([C:9]1[NH:10][C:11](=[O:21])[C:12]([OH:20])=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:14]=1)([CH3:8])[CH3:7].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:20][C:12]1[C:11](=[O:21])[N:10]2[CH2:2][CH2:3][O:4][CH2:5][C:6]([CH3:8])([CH3:7])[C:9]2=[N:14][C:13]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 136094113Ethyl 2-(1-(2-chloroethoxy)-2-methylpropan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Product 1

HCID 58877856Ethyl 3-hydroxy-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylateYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Ethyl 2-(1-(2-chloroethoxy)-2-methylpropan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (1.75 g, 5.49 mmol) was dissolved in 30 mL DMF under N2 and treated with K2CO3 (2.27 g, 16.5 mmol). This was warmed at 70-80° C. with stirring for 16 h. The DMF was evaporated at reduced pressure and the residue was dissolved in water and washed with Et2O. The aqueous layer was acidified with dil HCl and extracted with CH2Cl2. After drying (MgSO4), filtration and concentration a solid was obtained. Trituration from 1:1 Et2O/hexanes gave the title compound (1.2 g, 77%) as white solid. 1H NMR (300 MHz, CDCl3) δ: 1.35-1.45 (m, 9H), 3.58 (s, 2H), 3.60-4.10 (m, 1H), 4.41 (q, J=6.95 Hz, 2H), 4.30-4.82 (m, 2H), 10.42 (s, 1H). LC/MS (M+H): 283.

Workup

  1. customThe DMF was evaporated at reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washwashed with Et2O
  4. extractionextracted with CH2Cl2
  5. customAfter drying
  6. filtration(MgSO4), filtration and concentration a solid
  7. customwas obtained

Sources & evidence

ORD record
ord-10438f87402b4462889738422f97afd2
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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