Sodium ethoxide → 4-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

HRID 724007

Reaction equation

HRID 724007 reaction equation
CC[O-].[Na+].Cl.[CH:6]1([NH:11][C:12]([NH2:14])=[NH:13])[CH2:10][CH2:9][CH2:8][CH2:7]1.[Cl:15][C:16]1[CH:21]=[CH:20][N:19]2[N:22]=[C:23]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:24]([C:25](=O)[C:26]#[CH:27])=[C:18]2[CH:17]=1>C(O)C>[Cl:15][C:16]1[CH:21]=[CH:20][N:19]2[N:22]=[C:23]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[C:24]([C:25]3[CH:26]=[CH:27][N:14]=[C:12]([NH:11][CH:6]4[CH2:10][CH2:9][CH2:8][CH2:7]4)[N:13]=3)=[C:18]2[CH:17]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 221809211-[5-Chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, compound

Product 1

HCID 102238594-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamineYield 66.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethylate (0.7 mL (2.09 mmol), 210% in ethanol) and cyclopentyl guanidine hydrochloride (0.47 g, 2.88 mmol) were added sequentially to ethanol (30 mL). The resulting solution was stirred at room temperature for 30 minutes. 1-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-propyn-1-one (0.5 g, 1.61 mmol) was added, and the suspension was stirred at room temperature for 2 days. The reaction was quenched by the addition of water. The aqueous phase was extracted by ethyl acetate. The organics were combined, washed with brine and dried over magnesium sulfate. Filtration and concentration gave a solid. This solid was recrystallized from methanol to give 4-[5-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (0.45 g, 66%) as a pale yellow solid. 1H NMR (CDCl3) δ 8.59 (b, 1H), 8.42 (d, 1H), 8.05 (d, 1H), 7.59 (d, 2H), 7.03 (d, 2H), 6.91 (dd, 1H), 6.39 (d, 1H), 5.34 (broad s, 1H), 4.42 (m, 1H), 3.92 (s, 3H), 2.17 (m, 2H), 1.86–1.60 (m, 6H); MS m/z 420 (M+1).

Workup

  1. stirringthe suspension was stirred at room temperature for 2 days
  2. customThe reaction was quenched by the addition of water
  3. extractionThe aqueous phase was extracted by ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and concentration
  7. customgave a solid
  8. customThis solid was recrystallized from methanol

Sources & evidence

ORD record
ord-a65ee26c3d8f484dbd82136678d4d9d7
Source dataset
uspto-grants-2006_11
Patent number
US07141569B2

Linked notes

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