Potassium Carbonate → HCID 58314118, compound

HRID 624820Notes

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-57416c201fdd429d967a55f0295bc535
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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