Malononitrile → 7-Amino-5-(3-bromo-4,5-dimethoxy-phenyl)-2,4-dimethyl-5H-pyrano[2,3-d]pyrimidine-6-carbonitrile

HRID 2206278Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[CH:14]=O.[C:23](#[N:27])[CH2:24][C:25]#[N:26].C1N2CCN(CC2)C1>C(O)C.O>[NH2:27][C:23]1[O:1][C:2]2[N:3]=[C:4]([CH3:9])[N:5]=[C:6]([CH3:8])[C:7]=2[CH:14]([C:13]2[CH:16]=[C:17]([O:21][CH3:22])[C:18]([O:19][CH3:20])=[C:11]([Br:10])[CH:12]=2)[C:24]=1[C:25]#[N:26]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Hydroxy-2,6-dimethylpyrimidine (546 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 2 ml ethanol at room temperature, charged with DABCO (48.4 μl, 1.46 mmol) and then stirred at 80° C. under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for 1 h and the precipitates were separated by filtration. It was washed well with 50% aqueous ethanol and dried under vacuum (1.52 g, 3.64 mmol, 82.8%).

Workup

temperatureThe reaction mixture was then cooled down to room temperature
stirringstirred at room temperature for 1 h
customthe precipitates were separated by filtration
washIt was washed well with 50% aqueous ethanol
customdried under vacuum (1.52 g, 3.64 mmol, 82.8%)

Sources & evidence

ORD record: ord-a6c82628e2814ca98f2391cee6495021
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371333B2

Reaction notes

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