1,2-Dimethoxyethane → HCID 24905179, compound

HRID 238006Notes

Reaction equation

HRID 238006 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:12]([CH3:14])[CH3:13])[N:3]=1.[C:15]([O-:18])([O-])=O.[Na+].[Na+].CO[CH2:23][CH2:24][O:25][CH3:26]>CCO.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>[CH:12]([N:4]1[C:5]2=[N:6][CH:7]=[N:8][C:9]([NH2:11])=[C:10]2[C:2]([C:23]2[C:24]([O:25][CH3:26])=[N:6][C:5]([O:18][CH3:15])=[N:4][CH:12]=2)=[N:3]1)([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 249053373-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 24905179HCID 24905179, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution 2,4-dimethoxypyrimidin-5-yl-5-boronic acid (106 mg, 0.58 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (70 mg, 0.23 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 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 silica gel column chromatography [MeOH—CH2Cl2, 2:98] to yield BA66. ESI-MS (M+H)+ m/z calcd 316.1, found 316.0.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction was extracted with saturated NaCl and CH2Cl2
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel column chromatography [MeOH—CH2Cl2, 2:98]
  5. customto yield BA66

Sources & evidence

ORD record
ord-79c551915826495db02f0299c9bfade6
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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