2-Methoxyethylamine → 3-[2-(butylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)pyrazolo[1,5-a]pyridin-7-amine

HRID 1373816Notes

Reaction equation

HRID 1373816 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].[CH3:29][O:30][CH2:31][CH2:32][NH2:33]>>[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]([NH:33][CH2:32][CH2:31][O:30][CH3:29])=[CH:19][CH:18]=[CH:17][C:16]=23)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 22174847N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine

Product 1

HCID 52756943-[2-(butylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)pyrazolo[1,5-a]pyridin-7-amineYield 93%

Procedure

A mixture of N-butyl-4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinamine (56 mg, 0.14 mmol) and 2-methoxyethylamine (5 mL) was heated to reflux for 24 hours, then cooled and concentrated. Flash column chromatography eluting with 3:1 hexanes:ethyl acetate afforded 3-[2-(butylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)pyrazolo[1,5-α]pyridin-7-amine (57.1 mg, 93%) as a yellow foam. 1H NMR (CDCl3): δ 8.02 (d, 1H), 7.76 (d, 1H), 7.65 (m, 2H), 7.32 (t, 1H), 7.15 (t, 2H), 6.29 (m, 2H), 6.05 (d, 1H), 5.10 (broad, 1H), 3.72 (t, 2H), 3.57 (q, 2H), 3.47 (q, 2H), 3.43 (s, 3H), 1.69–1.44 (m, 4H), 0.98 (t, 3H); MS m/z 435 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. washFlash column chromatography eluting with 3:1 hexanes

Sources & evidence

ORD record
ord-07d25c56446c464b8fe7082ae4d025d0
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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