Potassium Carbonate → 4-Chloro-2-[(E)-2-phenylethenyl]-6H-pyrimido[5,4-b][1,4]oxazin-7(8H)-one

HRID 657094Notes

Reaction equation

[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10](OCC)=[O:11])=[C:6]([Cl:15])[N:5]=[C:4](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:15][C:6]1[C:7]2[O:8][CH2:9][C:10](=[O:11])[NH:1][C:2]=2[N:3]=[C:4](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:5]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of ethyl ({4-amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}oxy)acetate (0.55 g, 1.65 mmol) in DMF (5 mL) was added solid K2CO3 (0.46 g, 3.3 mmol) and the resulting mixture was heated at 75° C. for 1 h. The solvent was evaporated under reduced pressure and the residue was extracted with 10% methanol in DCM (3×100 ml). The organic extracts were combined, dried over anhydrous MgSO4, filtered and evaporated under reduced pressure to give a solid which was purified by column chromatography (silica gel) with a 0-10% methanol in DCM gradient to give the desired product as a solid (0.47 g, 99%).

Workup

customThe solvent was evaporated under reduced pressure
extractionthe residue was extracted with 10% methanol in DCM (3×100 ml)
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customevaporated under reduced pressure
customto give a solid which
customwas purified by column chromatography (silica gel) with a 0-10% methanol in DCM gradient

Sources & evidence

ORD record: ord-4e72eafb1c644758a7233ab2aee4b777
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071592B2

Reaction notes

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