Sodium Carbonate → 3-(3-Fluoro-4-methoxy-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

HRID 1396540Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:11])=[N:8][CH:9]=2)[N:4]([CH3:12])[N:3]=1.[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:13][C:14]1[CH:15]=[C:16]([C:2]2[C:10]3[C:5](=[N:6][C:7]([NH2:11])=[N:8][CH:9]=3)[N:4]([CH3:12])[N:3]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]

Participants

Conditions

Temperature: 70 °C

Procedure

3-Bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Intermediate 3) (1.2 g, 5.2 mmol) is dissolved in THF (40 ml), under an inert atmosphere of argon. To this is added Pd(PPh3)2Cl2 (0.224 g, 0.32 mmol), [3-fluoro-4-methoxyphenyl]boronic acid (0.98 g, 5.8 mmol) and a solution of Na2CO3 (1.5 g, 14 mmol) dissolved in distilled water (4 ml). The reaction mixture is heated to reflux at 70° C. for 24 hours. After cooling to room temperature the reaction mixture is pre-absorbed onto silica and purification by flash chromatography on silica eluting with iso-hexanes:EtOAc (2:1) affords the title compound as a solid.

Workup

temperatureThe reaction mixture is heated
temperatureAfter cooling to room temperature the reaction mixture
customis pre-absorbed onto silica and purification by flash chromatography on silica eluting with iso-hexanes:EtOAc (2:1)

Sources & evidence

ORD record: ord-559e06d239f4485e973716fa62bf871b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901134B2

Reaction notes

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