Dimethylformamide dimethyl acetal → Cyclopentyl methyl ether

HRID 590834Notes

Reaction equation

HRID 590834 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9]([I:31])=[N:10][N:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[CH:3]=1.[CH3:32][O:33][CH:34](OC)[N:35]([CH3:37])[CH3:36]>>[CH:25]1([O:33][CH3:32])[CH2:30][CH2:29][CH2:28][CH2:27]1.[Cl:1][C:2]1[N:7]=[C:6](/[CH:8]=[CH:34]/[N:35]([CH3:37])[CH3:36])[C:5]2[C:9]([I:31])=[N:10][N:11]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 1181689626-chloro-3-iodo-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridine2×

Product 2

HCID 138539Cyclopentyl methyl etherHCID 118272432(E)-2-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N,N-dimethylethenamine

Procedure

6-chloro-3-iodo-trityl-1H-pyrazolo[4.3-c]pyridine (Intermediate 1C, 2 g, 3.73 mmol), N, N-dimethylformamide-dimethyl acetal (DMF-DMA) (4.45 g, 37.3 mmol) were stirred at 125° C. for 12 hrs. Reaction was concentrated and excess DMF-DMA azeotroped with toluene. Trituration with cylopentylmethylether gave (E)-2-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N,N-dimethylethenamine. MS ESI calc'd. for C29H24ClIN4 [M+H]+ 591. found 591.

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. customexcess DMF-DMA azeotroped with toluene

Sources & evidence

ORD record
ord-8cc57f8246b24be5a48b78a85e7c3156
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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