Triethylamine → HCID 59635506, compound

HRID 383700Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([CH:11]=[O:12])=[C:4]2[N:3]=1.[C:13]([C:16]1[S:20][C:19](B(O)O)=[CH:18][CH:17]=1)([OH:15])=[O:14].C(N(CC)CC)C>CN(C=O)C>[CH:11]([C:10]1[CH:9]=[N:8][N:5]2[CH:6]=[CH:7][C:2]([C:19]3[S:20][C:16]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=3)=[N:3][C:4]=12)=[O:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To 5-chloropyrazolo[1,5-a]pyrimidine-3-carbaldehyde (590 mg, 3.25 mmol) in DMF was added 5-Carboxythiophene-2-boronic acid (670 mg, 3.9 mmol), triethylamine (1.13 mL, 8.11 mmol) and dichloro-((bis-diphenylphosphino)ferrocenyl)palladium(II) dichloromethane adduct (120 mg, 0.16 mmol). The reaction mixture was degassed with nitrogen then heated at 100° C. for 2 hours. The mixture was cooled to room temperature, diluted with 1N HCl, and filtered. The collected solid was washed with 1N HCl and dried under vacuum. The desired product, 5-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid, was recovered in 22% yield and used for the next step without further purification. LCMS (M+1=274)

Workup

customThe reaction mixture was degassed with nitrogen
temperatureThe mixture was cooled to room temperature
additiondiluted with 1N HCl
filtrationfiltered
washThe collected solid was washed with 1N HCl
customdried under vacuum
customThe desired product, 5-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid, was recovered in 22% yield
customused for the next step without further purification

Sources & evidence

ORD record: ord-c458f6ad621e4135b78eb5bc1a785b9a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367681B2

Reaction notes

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