N-methyl-2-pyrrolidone → HCID 17747619, compound

HRID 1037581Notes

Reaction equation

HRID 1037581 reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[C:18]#[C:19][C:20]1[CH:25]=[CH:24][N:23](NC)[CH2:22][N:21]=1.[CH3:28][N:29]1C(=O)CCC1>>[CH3:28][NH:29][C:22]1[N:21]=[C:20]([C:19]2[NH:7][C:8]3[C:9]([CH:18]=2)=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=3)[CH:25]=[CH:24][N:23]=1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidone2×HCID 23665647Potassium tert-butoxideHCID 69229367Methyl 4-amino-3-(1-methylaminopyrimidin-4-yl)ethynylbenzoate

Product 1

HCID 17747619HCID 17747619, compound

Procedure

73 mg (0.7 mmol) of potassium tert-butoxide were dissolved in 1 ml of NMP and admixed with a solution of 140 mg (0.5 mmol) of methyl 4-amino-3-(1-methylaminopyrimidin-4-yl)ethynylbenzoate in 1 ml of NMP. Subsequently, stirring was continued at RT for 24 h. Aqueous workup afforded 115 mg of methyl 2-(2-methylaminopyrimidin-4-yl)-1H-indole-5-carboxylate (HPLC: 92.3 area %).

Sources & evidence

ORD record
ord-370211b7171b491a8a674bec8961d1bf
Source dataset
uspto-grants-2013_10
Patent number
US08546567B2

Reaction notes

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