Acetonitrile → HCID 12004101, compound

HRID 971258Notes

Reaction equation

HRID 971258 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]([CH3:33])([CH3:32])[CH2:25][N:26]2[C:29](=[O:31])[CH3:30])=[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]([CH3:33])([CH3:32])[CH2:25][N:26]5[C:29](=[O:31])[CH3:30])=[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 218651761-(6-Amino-3,3-dimethylindolin-1-yl)ethanoneHCID 590214784-Chloro-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Product 1

HCID 12004101HCID 12004101, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4-chloro-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (40 mg, 0.14 mmol), 1-(6-amino-3,3-dimethylindolin-1-yl)ethanone (60 mg, 0.29 mmol), and acetonitrile (3 mL) was heated in a sealed tube via microwave at 180° C. for 60 min. The mixture was treated with EtOAc (50 mL) and saturated aqueous sodium bicarbonate. 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 an off-white 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-412e5b5c6c0e4f23b1cad564a8d9fc7b
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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