Dichloromethane → 4-(2-Amino-3-pyridin-2-yl-pyrazolo[1,5-a]pyrimidin-6-yl)-phenol

HRID 490112Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([NH2:17])[C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:7]=1.[OH:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+].ClCCl>CN(C=O)C>[NH2:17][C:9]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[C:5]2[N:4]=[CH:3][C:2]([C:22]3[CH:23]=[CH:24][C:19]([OH:18])=[CH:20][CH:21]=3)=[CH:7][N:6]2[N:8]=1

Participants

Conditions

Temperature: 120 °C

Procedure

6-Bromo-3-pyridin-2-yl-pyrazolo[1,5-a]pyrimidin-2-ylamine (50 mg, 0.17 mmol) and 4-hydroxyphenylboronic acid (48 mg, 0.35 mmol) were suspended in dry DMF (1.4 ml). Aqueous 2M Na2CO3 (0.346 mL, 0.69 mmol) was added and the reaction mixture was degassed. [1,1-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex in dichloromethane (1:1 ratio, 8 mg, 0.010 mmol) was added and the mixture was heated in a microwave at 120° C. for 20 minutes. After allowing the reaction to cool down to room temperature, the mixture was concentrated under reduced pressure. The resulting solid was purified by silica gel chromatography eluting with EtOAc to afford the title compound as a yellow solid (35 mg, 67% yield). MS (ES+) 304. δH (DMSO-d6) 6.8 (1H, d), 7.1 (3H, m), 7.2 (1H, d), 7.3 (1H, t), 7.9 (1H, t), 8.6 (2H, m), 8.8 (1H, s), 9.2 (1H, s), 9.7 (1H, s).

Workup

customthe reaction mixture was degassed
customthe reaction
temperatureto cool down to room temperature
concentrationthe mixture was concentrated under reduced pressure
customThe resulting solid was purified by silica gel chromatography
washeluting with EtOAc

Sources & evidence

ORD record: ord-088c231665174cf6a0cb7a2751e6de36
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528138B2

Reaction notes

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