Acetic Anhydride → HCID 66693303, compound
Reaction equation
[CH:1]1([C:4](=[O:27])[CH2:5][C:6]([C:8]2[C:13](=[O:14])[N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:10][CH:9]=2)=[O:7])[CH2:3][CH2:2]1.[CH:28](OCC)(OCC)[O:29][CH2:30][CH3:31].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[CH:1]1([C:4](=[O:27])[C:5](=[CH:28][O:29][CH2:30][CH3:31])[C:6]([C:8]2[C:13](=[O:14])[N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:10][CH:9]=2)=[O:7])[CH2:3][CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A suspension of 1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-1,3-propanedione (i.e. the product from Example 6, Step A) (165 mg, 0.46 mmol), triethyl orthoformate (0.23 mL, 1.4 mmol), and acetic anhydride (0.92 mL) was heated at 110° C. under a nitrogen atmosphere for 4 h. The residue was dissolved in toluene (5 mL) and the resulting solution was concentrated under reduced pressure at 50° C. The residue was re-dissolved in toluene (5 mL) and the resulting solution was concentrated at 50° C. to give 181 mg of the title compound as a brown oil that was used in the next step without further purification. 1H NMR analysis showed the product to contain a mixture of Z- and E-olefin isomers.
Workup
- concentrationthe resulting solution was concentrated under reduced pressure at 50° C
- dissolutionThe residue was re-dissolved in toluene (5 mL)
- concentrationthe resulting solution was concentrated at 50° C.
Sources & evidence
- ORD record
- ord-c9f5ad56bc074ef296893f4fc3df4ba9
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952024B2
Reaction notes
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