Methanol → 2-((4-Fluorobenzylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one

HRID 713390Notes

Reaction equation

HRID 713390 reaction equation
[NH2:1][CH2:2][C:3]1[NH:4][C:5](=[O:13])[C:6]2[CH2:12][O:11][CH2:10][CH2:9][C:7]=2[N:8]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1.CCCCCC.CO>C(O)C.ClCCl>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:1][CH2:2][C:3]2[NH:4][C:5](=[O:13])[C:6]3[CH2:12][O:11][CH2:10][CH2:9][C:7]=3[N:8]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 680214-Fluorobenzyl bromideHCID 1357418942-(Aminomethyl)-7,8-dihydro-3H-pyrano[4,3-D]pyrimidin-4(5H)-one

Product 1

HCID 1366272272-((4-Fluorobenzylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-oneYield 83.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (150 mg, 0.83 mmol) and 1-(bromomethyl)-4-fluorobenzene (83 μL 0.66 mmol) was heated via microwave in ethanol (5 mL) at 120° C. for 5 minutes. The reaction mixture was concentrated in vacuo and the residue was purified via flash column chromatography (ethyl acetate:hexane, 20:80 to 100:0 and then methanol: dichloromethane, 1:99 to 30:70) to provide the title compound (160 mg, 67% yield). MS m/z 290.2 (M+1), retention time=1.04 min

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified via flash column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-e073417856d64b9b84e82b3fd00ecd9b
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…