Sodium hydride → HCID 58203502, compound

HRID 2194777Notes

Reaction equation

HRID 2194777 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([C:13]#[N:14])[C:7]2[CH:8]=[CH:9][NH:10][C:11]=2[CH:12]=1.Cl[C:16]1[C:21]([CH:22]([CH3:24])[CH3:23])=[C:20]([O:25][CH3:26])[N:19]=[C:18]([O:27][CH3:28])[N:17]=1>CN(C=O)C.CCOC(C)=O>[CH:22]([C:21]1[C:16]([N:10]2[C:11]3[CH:12]=[C:4]([CH3:3])[CH:5]=[C:6]([C:13]#[N:14])[C:7]=3[CH:8]=[CH:9]2)=[N:17][C:18]([O:27][CH3:28])=[N:19][C:20]=1[O:25][CH3:26])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidineHCID 247288206-Methyl-1H-indole-4-carbonitrile

Product 1

HCID 58203502HCID 58203502, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

NaH (148 mg, 1.1 eq.) was added to 6-methyl-1H-indole-4-carbonitrile (526 mg, 3.37 mmol) in 20 mL of DMF. After 5 minutes, 4-chloro-5-isopropyl-2,6-dimethoxy-pyrimidine was added to the reaction mixture. The reaction mixture was heated at 50° C. for 5 hours. The reaction mixture was diluted with EtOAc and washed with brine. The organic layer was concentrated and purified (silica gel, 0-80% EtOAC/hexane) to give a white solid (470 mg, 42%). LC-MS shows 337.2 (M+1).

Workup

  1. washwashed with brine
  2. concentrationThe organic layer was concentrated
  3. custompurified (silica gel, 0-80% EtOAC/hexane)

Sources & evidence

ORD record
ord-5accba48345f413abc38d9e7cf75ceb1
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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