Morpholine → (2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl acetate

HRID 1043558Notes

Reaction equation

HRID 1043558 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]=[C:11]([Cl:17])[N:12]=[C:13](Cl)[C:14]=2[N:15]=1)(=[O:3])[CH3:2].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(O)C>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]=[C:11]([Cl:17])[N:12]=[C:13]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:14]=2[N:15]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 156970Pyrido(3,2-d)pyrimidine-6-methanol, 2,4-dichloro-, acetate (ester)

Product 1

HCID 86657075(2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl acetateYield 96.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2,4-dichloropyrido[3,2-d]pyrimidin-6-yl)methyl acetate (1.92 g, 7.06 mmol) according to Srinivasan and Broom (1981) J. Org. Chem. 46:1777-1781, and morpholine (1.3 mL, 14.9 mmol) in ethanol (100 mL) was stirred at room temperature for 2 hours. The reaction mixture was then evaporated to dryness. The crude product was purified by flash chromatography (DCM) to give (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl acetate 5 (2.2 g, 96%). 1H-NMR (CDCl3): δ 8.05 (d, 1H), 7.66 (d, 1H), 5.29 (s, 2H), 4.5 (s, br, 4H), 3.87 (m, 4H), 2.19 (s, 3H)

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. customThe crude product was purified by flash chromatography (DCM)

Sources & evidence

ORD record
ord-787ce8ebbf3a4da1a1b33968ee0cfc9d
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

Loading…