Water → HCID 86714605, compound

HRID 624758Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[S:13][CH:12]=[C:11]([C:14]2[CH:19]=[C:18]([NH:20][CH:21]3[CH2:23][CH2:22]3)[N:17]3[N:24]=[CH:25][C:26]([CH:27]=[O:28])=[C:16]3[N:15]=2)[CH:10]=1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.O>CN(C=O)C>[CH:21]1([NH:20][C:18]2[N:17]3[N:24]=[CH:25][C:26]([CH:27]=[O:28])=[C:16]3[N:15]=[C:14]([C:11]3[CH:10]=[C:9]([CH2:8][N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[S:13][CH:12]=3)[CH:19]=2)[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 50 °C

Procedure

Potassium carbonate (30 mg, 0.20 mmol) was added to 5-(5-(bromomethyl)thiophen-3-yl)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (25 mg, 0.07 mmol) dissolved in DMF (0.7 mL). Pyrrolidine (6 μL, 0.07 mmol) was added and the reaction was heated to 50° C. for 1.25 h. Water (3 mL) was added and the orange precipitate was filtered and dried in vacuo to give 7-(cyclopropylamino)-5-(5-(pyrrolidin-1-ylmethyl)thiophen-3-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (13 mg, 54%) which was used without further purification. LCMS (ES): >85% pure, m/z 368 [M+1]+.

Workup

filtrationthe orange precipitate was filtered
customdried in vacuo

Sources & evidence

ORD record: ord-b309da9c02f44e89bd97a67ef203549f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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