Potassium Carbonate → HCID 58314118, compound

HRID 2037037Notes

Reaction equation

[N:1]1([C:7]2[N:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]#[N:10])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:16]1[CH:21]=[C:20]([NH:22][CH:23]2[CH2:25][CH2:24]2)[N:19]2[N:26]=[CH:27][C:28]([CH:29]=[O:30])=[C:18]2[N:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:23]1([NH:22][C:20]2[N:19]3[N:26]=[CH:27][C:28]([CH:29]=[O:30])=[C:18]3[N:17]=[C:16]([N:4]3[CH2:3][CH2:2][N:1]([C:7]4[N:14]=[CH:13][CH:12]=[CH:11][C:8]=4[C:9]#[N:10])[CH2:6][CH2:5]3)[CH:21]=2)[CH2:24][CH2:25]1

Participants

Conditions

Temperature: 95 °C

Procedure

In a reaction flask, 2-(piperazin-1-yl)nicotinonitrile (22 mg, 0.11 mmol) was mixed with 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (27 mg, 0.11 mmol) in DMF (0.5 mL) along with potassium carbonate (32 mg, 0.23 mmol). The reaction was heated at 95° C. for 12 hours then partitioned between water and ethyl acetate. The organic layer was washed with water then saturated NaCl solution. The ethyl acetate layer was isolated, dried of anhydrous sodium sulfate, filtered, and evaporated to dryness. The product, 2-(4-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)nicotinonitrile, was recovered in 35% yield (16 mg) after recrystallization from ethyl acetate/hexanes. LCMS (M+1=389)

Workup

customthen partitioned between water and ethyl acetate
washThe organic layer was washed with water
customThe ethyl acetate layer was isolated
dry with materialdried of anhydrous sodium sulfate
filtrationfiltered
customevaporated to dryness
customThe product, 2-(4-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)nicotinonitrile, was recovered in 35% yield (16 mg)
customafter recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-faf838492e2f4e8b8086341f50d5b9c3
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575177B2

Reaction notes

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