Dimethylformamide dimethyl acetal → N'-[5-[5-(3-Dimethylamino-acryloyl)-2-isopropyl-4-methoxy-phenoxy]-4-(dimethylamino-methyleneamino)-pyrimidin-2-yl]-N,N-dimethyl-formamidine

HRID 38389Notes

Reaction equation

HRID 38389 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][C:10]2[C:11]([CH:21]([CH3:23])[CH3:22])=[CH:12][C:13]([O:19][CH3:20])=[C:14]([C:16](=[O:18])[CH3:17])[CH:15]=2)=[CH:4][N:3]=1.CO[CH:26](OC)[N:27]([CH3:29])[CH3:28]>CN(C)C=O>[CH3:26][N:27]([CH3:29])[CH:28]=[CH:17][C:16]([C:14]1[C:13]([O:19][CH3:20])=[CH:12][C:11]([CH:21]([CH3:23])[CH3:22])=[C:10]([CH:15]=1)[O:9][C:5]1[C:6]([N:8]=[CH:26][N:27]([CH3:29])[CH3:28])=[N:7][C:2]([N:1]=[CH:26][N:27]([CH3:29])[CH3:28])=[N:3][CH:4]=1)=[O:18]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 573300761-[5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-ethanone

Product 1

HCID 67053447N'-[5-[5-(3-Dimethylamino-acryloyl)-2-isopropyl-4-methoxy-phenoxy]-4-(dimethylamino-methyleneamino)-pyrimidin-2-yl]-N,N-dimethyl-formamidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
114 °C

Procedure

To 1-[5-(2,4-diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-phenyl]-ethanone (100 mg, 0.32 mmol, from Example 16) dissolved in anhydrous N,N-dimethylformamide (0.6 mL) was added N,N-dimethylformamide dimethyl acetal (0.17 mL, 1.26 mmol) and the reaction was heated at 114° C. overnight. Concentration of the reaction mixture yielded N′-[5-[5-(3-Dimethylamino-acryloyl)-2-isopropyl-4-methoxy-phenoxy]-4-(dimethylamino-methyleneamino)-pyrimidin-2-yl]-N,N-dimethyl-formamidine.

Sources & evidence

ORD record
ord-fba9ffa40c08453297dc018a28d1053f
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

Loading…