Acetonitrile → 6-(7-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-ylamino)-3,3-dimethylindolin-2-one

HRID 971255Notes

Reaction equation

HRID 971255 reaction equation
Cl[C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:19][C:20]1[CH:28]=[C:27]2[C:23]([C:24]([CH3:31])([CH3:30])[C:25](=[O:29])[NH:26]2)=[CH:22][CH:21]=1.C(#N)C.C([O-])(O)=O.[Na+]>CCOC(C)=O>[Cl:18][C:17]1[C:12]([N:9]2[CH2:10][CH2:11][C:3]3[C:2]([NH:19][C:20]4[CH:28]=[C:27]5[C:23]([C:24]([CH3:31])([CH3:30])[C:25](=[O:29])[NH:26]5)=[CH:22][CH:21]=4)=[N:7][CH:6]=[N:5][C:4]=3[CH2:8]2)=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 135892296-Amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-oneHCID 590214784-Chloro-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Product 1

HCID 120041006-(7-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-ylamino)-3,3-dimethylindolin-2-oneYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of the 4-chloro-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (50 mg, 0.18 mmol), 6-amino-3,3-dimethylindolin-2-one (63 mg, 0.36 mmol), and acetonitrile (3 mL) was heated in a sealed tube via at 180° C. for 60 min. The mixture was treated with EtOAc (50 mL) and sat. aq. solution of NaHCO3. The organic layer was separated and washed with brine, dried (Na2SO4), and evaporated. The residue was purified by flash chromatography over silica gel to give a light yellow solid (50 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-58e062ab00a443a892036a2cba5f9fc3
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

Loading…