2-(Tri-n-butylstannyl)oxazole → HCID 74767290, compound

HRID 923305Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[N:9]=[CH:10][C:3]=12.C([Sn](CCCC)(CCCC)[C:24]1[O:25][CH:26]=[CH:27][N:28]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:13]1([CH2:12][CH2:11][N:8]2[C:4]3=[N:5][CH:6]=[N:7][C:2]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[C:3]3[CH:10]=[N:9]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-1-(2-(piperidin-1-yl)ethyl)-1H-pyrazolo[3,4-d]pyrimidine (50 mg, 0.188 mmol), 2-(tri-n-butylstannyl)oxazole (0.059 ml, 0.282 mmol) in toluene (3 mL) was introduced in a microwave vial. It was degassed by argon for 30 minutes followed by the addition of Pd(Ph3P)4 (22 mg, 19 mmol) after which the mixture was degassed for 10 additional minutes. The mixture was stirred at 100° C. for 30 min under microwave irradiation (150 W). The solvent was removed and the crude thus obtained was purified by flash chromatography to provide 2-(1-(2-(piperidin-1-yl)ethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)oxazole as a cream-colored solid (37 mg, 0.12 mmol, 66%).

Workup

additionwas introduced in a microwave vial
customIt was degassed by argon for 30 minutes
customwas degassed for 10 additional minutes
customThe solvent was removed
customthe crude thus obtained
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-3afaa2ebc1954e24bbefc0dd2bd99b7c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278974B2

Reaction notes

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