Dimethylformamide dimethyl acetal → N'-[6-(2,6-dichlorophenyl)-2-{3-(diethylamino)propylamino}-pyrido[2,3-d]pyrimidin-7-yl]-N,N-dimethylformamidine

HRID 3450

Reaction equation

HRID 3450 reaction equation
[NH2:1][C:2]1[C:3]([C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:28])=[CH:4][C:5]2[CH:10]=[N:9][C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[N:7][C:6]=2[N:20]=1.[CH3:29][N:30]([CH:32](OC)OC)[CH3:31]>CN(C=O)C>[Cl:28][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([Cl:27])[C:21]=1[C:3]1[C:2]([N:1]=[CH:29][N:30]([CH3:32])[CH3:31])=[N:20][C:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[N:9]=[CH:10][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 53281146-(2,6-dichlorophenyl)-2-N-[3-(diethylamino)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine

Product 1

HCID 5328174N'-[6-(2,6-dichlorophenyl)-2-{3-(diethylamino)propylamino}-pyrido[2,3-d]pyrimidin-7-yl]-N,N-dimethylformamidineYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 210 mg (1 mmol) of 7-amino-6-(2,6-dichlorophenyl)-2-[3-(diethylamino) propylamino]-pyrido[2,3-d]pyrimidine from Example 20 in 0.8 mL of DMF was added 0.8 mL of DMF dimethyl acetal. The mixture was stirred at room temperature for 5.5 hours, then concentrated in vacuo. The residual oil was distributed between dichloromethane and water. The organic phase was dried over magnesium sulfate, then concentrated to a glass that was crystallized from acetonitrile to give 160 mg (68%) of N'-[6-(2,6-dichlorophenyl)-2-{3-(diethylamino) propylamino}-pyrido[2,3-d]pyrimidin-7-yl]-N, N-dimethylformamidine, mp 100°-104° C.

Workup

  1. concentrationconcentrated in vacuo
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated to a glass that
  4. customwas crystallized from acetonitrile

Sources & evidence

ORD record
ord-3b18944e08c244489c0c882a36845a09
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Linked notes

Loading…