Water → 1-(2-butylsulfanyl-pyrimidin-4-yl)-1H-indole-3-carboxylic acid amide

HRID 1947057Notes

Reaction equation

HRID 1947057 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([NH2:14])=[O:13])=[CH:4]1.[CH2:15]([S:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[CH:22][N:21]=1)[CH2:16][CH2:17][CH3:18].O>CN(C=O)C>[CH2:15]([S:19][C:20]1[N:21]=[C:22]([N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]([NH2:14])=[O:13])=[CH:4]2)[CH:23]=[CH:24][N:25]=1)[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 21925421H-indole-3-carboxamideHCID 597434972-Butylsulfanyl-4-chloro-pyrimidine

Product 1

HCID 693084491-(2-butylsulfanyl-pyrimidin-4-yl)-1H-indole-3-carboxylic acid amideYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (480 mg, 12 mmol, 60% suspension) was added to a solution of 1H-indole-3-carboxylic acid amide (1.6 g, 10 mmol) in DMF (5 mL) at 0° C. and stirred for 20 min. A solution of 2-butylsulfanyl-4-chloro-pyrimidine (2.23 g) in DMF (5 mL) was added at 0° C., and the mixture allowed to warm to RT overnight. Water was added to the mixture, and the resulting white solid filtered off, washed with water (20 mL) and DCM (20 mL) and air-dried overnight to provide 1-(2-butylsulfanyl-pyrimidin-4-yl)-1H-indole-3-carboxylic acid amide (3.224 g, 98.77% yield) as a crude product.

Workup

  1. filtrationthe resulting white solid filtered off
  2. washwashed with water (20 mL) and DCM (20 mL)
  3. customair-dried overnight

Sources & evidence

ORD record
ord-c39dde2ab05640d4a63ddff920e05a50
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

Loading…