Dimethylformamide dimethyl acetal → N'-[6-(2,6-dichlorophenyl)-7-[(dimethylamino)-methyleneamino]-pyrido[2,3-d]pyrimidin-2-yl]-N,N-dimethylformamidine

HRID 3452

Reaction equation

HRID 3452 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9]([NH2:20])=[N:8][C:6]=2[N:7]=1.[CH3:21][N:22]([CH:24](OC)OC)[CH3:23]>>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C:10]1[C:9]([N:20]=[CH:21][N:22]([CH3:24])[CH3:23])=[N:8][C:6]2[N:7]=[C:2]([N:1]=[CH:21][N:22]([CH3:24])[CH3:23])[N:3]=[CH:4][C:5]=2[CH:11]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 53281136-(2,6-Dichlorophenyl)pyrido[2,3-d]pyrimidine-2,7-diamine

Product 1

HCID 54482161N'-[6-(2,6-dichlorophenyl)-7-[(dimethylamino)-methyleneamino]-pyrido[2,3-d]pyrimidin-2-yl]-N,N-dimethylformamidine

Procedure

2,7-Diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine from Example 1 was reacted with DMF dimethyl acetal for 23 hours as described in Example 78. Workup as described above followed by purification on flash silica gel chromatography eluting sequentially with 100:0, 9:1, 4:1, and 7:3 ethyl acetate:methanol gave an oil that was crystallized from ethyl acetate to afford N'-[6-(2,6-dichlorophenyl)-7-[(dimethylamino)-methyleneamino]-pyrido[2,3-d]pyrimidin-2-yl]-N,N-dimethylformamidine, mp 269°-272° C.

Workup

  1. customabove followed by purification on flash silica gel chromatography
  2. washeluting sequentially with 100:0, 9:1, 4:1, and 7:3 ethyl acetate
  3. custommethanol gave an oil that
  4. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-a307a99b72164a51b19fd145458a144d
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Linked notes

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