4-Methoxybenzylamine → 4-Chloro-7-(4-methoxy-benzyl)-5-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

HRID 1192430Notes

Reaction equation

HRID 1192430 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH3:15])[CH2:9]OS(C)(=O)=O)=[C:6]([Cl:16])[N:5]=[CH:4][N:3]=1.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>C(Cl)Cl>[Cl:16][C:6]1[C:7]2[CH:8]([CH3:15])[CH2:9][N:24]([CH2:23][C:22]3[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)[C:2]=2[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 86598740Methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-propyl ester

Product 1

HCID 865987414-Chloro-7-(4-methoxy-benzyl)-5-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidineYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-propyl ester (0.54 g, 1.89 mmol) in DCM (30 mL) and TEA (4 mL) was added 4-methoxybenzyl amine (0.80 g, 5.83 mmol). The mixture was refluxed overnight. After cooling, the solvent was removed and the residue was subject to column chromatography, eluted by hexane/ethyl acetate (4:1) to give 4-Chloro-7-(4-methoxy-benzyl)-5-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (0.55 g, 99%). 1H NMR (CDCl3, 400 MHz) δ 8.24 (s, 1H), 7.17 (d, J=7.6 Hz, 2H), 6.86 (d, J=7.6 Hz, 2H), 4.55 (s, 2H), 3.80 (s, 3H), 3.66 (m, 1H), 3.37 (m, 1H), 3.07 (m, 1H), 1.31 (dd, J=7.2 Hz, J=1.2 Hz, 3H). MS (APCI+) [M+H]+291.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureAfter cooling
  3. customthe solvent was removed
  4. washeluted by hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-d656d8aa168b4256b8bd7f71a4746b26
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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