Methylamine → Ethyl 2-[2-(methylamino)pyrimidin-4-yl]-1H-indole-5-carboxylate

HRID 1037577Notes

Reaction equation

HRID 1037577 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:11]=3)[CH:5]=[CH:4][N:3]=1.[CH3:22][NH2:23]>C(O)C>[CH3:22][NH:23][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:11]=3)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59800134HCID 59800134, compound

Product 1

HCID 59800135Ethyl 2-[2-(methylamino)pyrimidin-4-yl]-1H-indole-5-carboxylateYield 105.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

30 g (95.4 mmol) of ethyl 2-(2-chloropyrimidin-4-yl)-1H-indole-5-carboxylate were initially charged and suspended in 150 ml of ethanol. 53.9 g of methylamine solution in ethanol (8 M) were added to this suspension which was heated to from 75° C. to 80° C. in an autoclave for 4 h. After concentration and washing with ethanol, 29.7 g of ethyl 2-(2-methylamino-pyrimidin-4-yl)-1H-indole-5-carboxylate were obtained (97.6 HPLC area %). LCMS: [M+H]⊕ 297.12

Workup

  1. temperaturewas heated to from 75° C. to 80° C. in an autoclave for 4 h
  2. concentrationAfter concentration
  3. washwashing with ethanol

Sources & evidence

ORD record
ord-69204989a4a949b8b7e5f4986ab89c4e
Source dataset
uspto-grants-2013_10
Patent number
US08546567B2

Reaction notes

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