Allylamine → N-allyl-3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amine

HRID 1373822Notes

Reaction equation

HRID 1373822 reaction equation
[CH2:1]([NH:5][C:6]1[N:11]=[C:10]([C:12]2[C:13]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[N:14][N:15]3[C:20](Cl)=[CH:19][CH:18]=[CH:17][C:16]=23)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].[CH2:29]([NH2:32])[CH:30]=[CH2:31]>>[CH2:29]([NH:32][C:20]1[N:15]2[N:14]=[C:13]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:12]([C:10]3[CH:9]=[CH:8][N:7]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:11]=3)=[C:16]2[CH:17]=[CH:18][CH:19]=1)[CH:30]=[CH2:31]

Participants

3

Reactant 2

HCID 7853AllylamineHCID 22174847N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine

Product 1

HCID 5275683N-allyl-3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-7-amineYield 88.5%

Procedure

A solution of N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinamine (0.15 g, 0.38 mmol) in allylamine (5 mL, 67 mmol) was heated at 85° C. in a sealed tube for 88 hours. After cooling and concentrating the reaction mixture, flash chromatography (4:1 hexanes-ethyl acetate) afforded N-allyl-3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (0.14 g, 88%) as a pale yellow foam. 1H NMR (CDCl3): δ 7.89 (broad, 1H), 7.78 (d, 1H), 7.62 (m, 2H), 7.36 (t, 1H), 7.16 (t, 2H), 6.31–6.26 (m, 2H), 6.09–5.92 (m, 2H), 5.39–5.24 (m, 2H), 4.06 (t, 2H), 3.50 (q, 2H), 1.72–1.41 (m, 4H), 0.98 (t, 3H); 19F NMR (CDCl3) δ −113.16; MS m/z 417 (M+1); Anal. Calcd for C24H25FN6: C, 69.21; H, 6.05; N, 20.18. Found: C, 69.27; H, 6.07; N, 20.03.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrating the reaction mixture, flash chromatography (4:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-ea38b664eb99440b86f0788899332e43
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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