Sodium Carbonate → HCID 24905157, compound

HRID 731782Notes

Reaction equation

[CH:1]([C:3]1[S:7][C:6](B(O)O)=[C:5]([CH3:11])[CH:4]=1)=O.IC1[C:21]2[C:16](=[N:17][CH:18]=[N:19][C:20]=2[NH2:22])[N:15]([CH:23]([CH3:25])[CH3:24])[N:14]=1.[C:26]([O-])([O-])=[O:27].[Na+].[Na+]>CCO.COCCOC.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>[NH2:22][C:20]1[N:19]=[CH:18][N:17]=[C:16]2[N:15]([CH:23]([CH3:25])[CH3:24])[N:14]=[C:1]([C:3]3[S:7][C:6]([CH:26]=[O:27])=[C:5]([CH3:11])[CH:4]=3)[C:21]=12

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 5-Formyl-3-methylthiophene-2-boronic acid (26 mg, 0.14 mmol) in EtOH (3.3 mL) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (40 mg, 0.13 mmol) in DME (12 mL). Pd(PPh3)4 (16 mg, 0.014 mmol) and saturated Na2CO3 (1.9 mL) were added and the reaction was heated to 80° C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA34 (14.7 mg, 38% yield). ESI-MS (M+H)+ m/z calcd 302.1, found 302.0.

Workup

temperatureAfter cooling
extractionthe reaction was extracted with saturated NaCl and CH2Cl2
concentrationconcentrated in vacuo
custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)
customto yield BA34 (14.7 mg, 38% yield)

Sources & evidence

ORD record: ord-c7cc0d56b8d54cd5a1d3cd9f551ac51b
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585868B2

Reaction notes

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