Water → 7-(Cyclopropylmethyl)-9-(2,4-dimethoxybenzyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,9-dihydro-8H-purin-8-one

HRID 510061Notes

Reaction equation

HRID 510061 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:4]=1[CH2:5][N:6]1[C:14](=[O:15])[NH:13][C:12]2[C:7]1=[N:8][C:9]([C:16]1[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:17]=1)=[N:10][CH:11]=2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:46][CH:47]1[CH2:49][CH2:48]1.O>CN(C=O)C>[CH:47]1([CH2:46][N:13]2[C:12]3[C:7](=[N:8][C:9]([C:16]4[C:24]5[C:19](=[N:20][CH:21]=[CH:22][CH:23]=5)[N:18]([CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[F:32])[N:17]=4)=[N:10][CH:11]=3)[N:6]([CH2:5][C:4]3[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:3]=3[O:2][CH3:1])[C:14]2=[O:15])[CH2:49][CH2:48]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 666350859-(2,4-Dimethoxybenzyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,9-dihydro-8H-purin-8-one

Product 1

HCID 666141447-(Cyclopropylmethyl)-9-(2,4-dimethoxybenzyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7,9-dihydro-8H-purin-8-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg (0.980 mmol) of the compound from example 82A were dissolved in 10 ml of DMF, 414 mg (1.270 mmol) of cesium carbonate and 150 mg (1.08 mmol) of 2-bromomethylcyclopropane were added and the mixture was stirred at RT for 18 h. Water was added and the mixture was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated on a rotary evaporator. The residue was dried under high vacuum. 482 mg (72% of theory, purity 82%) of the title compound were obtained.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated on a rotary evaporator
  4. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-21e175f7878c4c3eaf2836c1c12195a2
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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