Water → 6-Chloro-N-(3-methyl-1H-indol-1-yl)-N-propyl-4-pyrimidinamine

HRID 1646396Notes

Reaction equation

HRID 1646396 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([NH:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH3:20])=[CH:12]2)[CH:5]=1.Br[CH2:22][CH2:23][CH3:24].O>CN(C)C=O>[Cl:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([N:10]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH3:20])=[CH:12]2)[CH2:22][CH2:23][CH3:24])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 151582466-Chloro-N-(3-methyl-1H-indol-1-yl)-4-pyrimidinamine

Product 1

HCID 198020286-Chloro-N-(3-methyl-1H-indol-1-yl)-N-propyl-4-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of NaH (60% in oil, 1.52 g) in 40 ml dimethylformamide (hereafter DMF) at ice bath temperature was added 9.0 g of 6-chloro-N-(3-methyl-1H-indol-1-yl)-4-pyrimidinamine dropwise, in 50 ml DMF. After addition was complete, the reaction was stirred for 5 minutes and then 3.45 ml of 1-bromopropane was added dropwise to the cool mixture. Reaction was allowed to proceed for 4 hours at room temperature. The mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried (sat. NaCl, anhy. MgSO4).

Workup

  1. additionAfter addition
  2. customReaction
  3. waitto proceed for 4 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried (sat. NaCl

Sources & evidence

ORD record
ord-c354e118fa89477eaccaad07fa2d7d6a
Source dataset
uspto-grants-1993_01
Patent number
US05179204

Reaction notes

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