1,1'-Carbonyldiimidazole → 6-bromo-3-(2-methoxyethyl)-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-one

HRID 1826024Notes

Reaction equation

[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[C:19]([CH2:20][NH:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:18][C:17]([Br:26])=[CH:16][N:15]=1>ClCCCl>[Br:26][C:17]1[CH:16]=[N:15][C:14]2[NH:13][C:1](=[O:2])[N:21]([CH2:22][CH2:23][O:24][CH3:25])[CH2:20][C:19]=2[CH:18]=1

Participants

Conditions

Temperature: 65 °C

Procedure

1,1′-Carbonyldiimidazole (0.74 g, 4.60 mmole) was added to a solution of 2-amino-5-bromo-3-[(2-methoxyethyl)aminomethyl]pyridine (1.00 g, 3.80 mmole) in 1,2-dichloroethane (35 mL) at RT. The reaction was heated at 65° C. with stirring overnight, then was concentrated in vacuo. Flash chromatography on silica gel (5% MeOH/(CHCl3) gave title compound (0.90 g, 83%) as a yellow solid after drying in vacuo: MS (ES) m/e 286/288 (M+H)+.

Workup

concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-49a45874a11d4ffea4e0af571bf404c8
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049310B2

Reaction notes

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