Potassium Carbonate → HCID 10109870, compound

HRID 271607Notes

Reaction equation

HRID 271607 reaction equation
C1([C:7]2[CH:17]=[CH:16][CH:15]=[C:9]3[C:10]([NH:12][C:13](=[O:14])[C:8]=23)=[O:11])C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][C:26]1[N:36]([CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C:29]2[N:30]=[C:31]([C:34]#[N:35])[N:32]=[CH:33][C:28]=2[CH:27]=1>CN(C=O)C>[CH3:39][C:38]([CH3:41])([CH3:40])[CH2:37][N:36]1[C:29]2[N:30]=[C:31]([C:34]#[N:35])[N:32]=[CH:33][C:28]=2[CH:27]=[C:26]1[CH2:25][N:12]1[C:13](=[O:14])[C:8]2[C:9](=[CH:15][CH:16]=[CH:17][CH:7]=2)[C:10]1=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113128256-Bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrileHCID 15813860HCID 15813860, compound

Product 1

HCID 10109870HCID 10109870, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 500 mg (1.63 mmoles) of phenylphthalimide in 20 ml of DMF, 315 mg (2.28 mmoles) of K2CO3 and 500 mg (1.63 mmoles) of 6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile are added successively and the mixture is stireed for 2 hours at ambient temperature. The reaction mixture is quenched with ice-water and extracted with AcOEt. The combined extracts are washed with H2O, brine and dried over MgSO4. Chromatography on silica gel (eluent: n-Hexane:AcOEt=2:1) give 412 mg of desired 7-(2,2-dimethyl-propyl)-6-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 68% yield.

Workup

  1. customThe reaction mixture is quenched with ice-water
  2. extractionextracted with AcOEt
  3. washThe combined extracts are washed with H2O, brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-7585396faa0f430e898aa1932bbffcd1
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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