Sodium hydride → HCID 69311915, compound

HRID 1947024Notes

Reaction equation

HRID 1947024 reaction equation
[H-].[Na+].[CH:3]([Si:6]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][NH:12]2)([CH3:5])[CH3:4].Cl[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([S:30][CH3:31])[N:25]=1>CN(C=O)C>[CH3:31][S:30][C:26]1[N:27]=[C:28]([N:12]2[C:13]3[C:9](=[C:8]([O:7][Si:6]([CH:3]([CH3:5])[CH3:4])([CH:17]([CH3:19])[CH3:18])[CH:20]([CH3:22])[CH3:21])[CH:16]=[CH:15][CH:14]=3)[CH:10]=[CH:11]2)[CH:29]=[CH:24][N:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidineHCID 15307470HCID 15307470, compound

Product 1

HCID 69311915HCID 69311915, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (1.826 g) was added to DMF (400 mL) and cooled to 0° C. 4-(Triisopropyl-silyloxy)-1H-indole (12 g) was added portionwise at 0° C., and allowed to stir at 0° C. for 1 h. 4-Chloro-2-methylsulfanyl-pyrimidine (5.28 mL) was added dropwise, and the reaction mixture stirred at 0° C. for 4 h and then quenched with water. The aqueous layer was acidified with 1N HCl. The organic layer was extracted into DCM, and dried over sodium sulfate, filtered and the filtrate was concentrated and purified on a column with 100% hexane to 25% EtOAc/hexane to yield 1-(2-methylsulfanyl-pyrimidin-4-yl)-4-triisopropylsilanyloxy-1H-indole (11 g).

Workup

  1. stirringthe reaction mixture stirred at 0° C. for 4 h
  2. customquenched with water
  3. extractionThe organic layer was extracted into DCM
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. custompurified on a column with 100% hexane to 25% EtOAc/hexane

Sources & evidence

ORD record
ord-371c58d3b89a46d790d214f308dc1045
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

Loading…