Sodium ethoxide → HCID 10172841, compound

HRID 1296710Notes

Reaction equation

HRID 1296710 reaction equation
Cl.[CH:2]1([NH:7][C:8]([NH2:10])=[NH:9])[CH2:6][CH2:5][CH2:4][CH2:3]1.[O-]CC.[Na+].[Cl:15][C:16]1[CH:17]=[C:18]([C:22]2[C:30]([C:31](=O)[C:32]#[CH:33])=[C:29]3[N:24]([CH:25]=[N:26][CH:27]=[CH:28]3)[N:23]=2)[CH:19]=[CH:20][CH:21]=1>C(O)C.O>[Cl:15][C:16]1[CH:17]=[C:18]([C:22]2[C:30]([C:31]3[CH:32]=[CH:33][N:10]=[C:8]([NH:7][CH:2]4[CH2:6][CH2:5][CH2:4][CH2:3]4)[N:9]=3)=[C:29]3[N:24]([CH:25]=[N:26][CH:27]=[CH:28]3)[N:23]=2)[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 85865908HCID 85865908, compoundHCID 178479367HCID 178479367, compound

Product 1

HCID 10172841HCID 10172841, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a mixture of cyclopentyl guanidine hydrochloride (1.05g, 6.43 mmol) in ethanol (60 mL) was added sodium ethoxide (2.15 mL, 3 M in ethanol, 6.43 mmol). The mixture was stirred at room temperature for 30 minutes then cooled to 0° C. A solution of 1-[2-(3-chlorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]-2-propyn-1-one (1.4 g, 4.97 mmol) in ethanol (100 mL) was added and the reaction mixture was stirred at room temperature 16 hours. The reaction mixture was diluted with water (200 mL) then concentrated to about two thirds the original volume. The precipitated solids were collected on a filter to provide 4-[2-(3-Chlorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]-N-cyclopentylpyrimidin-2-amine (1.25 g, 64%) as a white solid. Rf 0.19 (4:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ9.32 (s,1H), 8.22 (d,1H), 8.13 (d, 1H), 8.01 (d, 1H), 7.72 (s,1H), 7.55–7.39 (m, 3H), 6.38 (d,1H), 5.19 (d, 1H), 4.33 (m, 1H), 2.08 (m, 2H), 1.80–1.52 (m, 6H); MS m/z 391 (M+1).

Workup

  1. temperaturethen cooled to 0° C
  2. stirringthe reaction mixture was stirred at room temperature 16 hours
  3. concentrationthen concentrated to about two thirds the original volume
  4. customThe precipitated solids were collected on
  5. filtrationa filter

Sources & evidence

ORD record
ord-8e5752a7d25943c68125f6504ed7e82b
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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