4-Methoxybenzylamine → 4-chloro-7-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

HRID 1192425Notes

Reaction equation

HRID 1192425 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH2:9]OS(C)(=O)=O)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>ClCCCl>[Cl:15][C:6]1[C:7]2[CH2:8][CH2:9][N:23]([CH2:22][C:21]3[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[C:2]=2[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 86598737Methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl ester

Product 1

HCID 529881474-chloro-7-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidineYield 71%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl ester (0.50 g, 1.84 mmol) and 4-methoxybenzylamine (0.60 g, 4.37 mmol) in DCE (30 mL) and TEA (4 mL) 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)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (0.36 g, 71%). 1H NMR (CDCl3, 400 MHz) δ 8.35 (s, 1H), 7.26 (dd, J=2.8 Hz, J=1.6 Hz, 2H), 6.88 (d, J=4.4 Hz, 2H), 5.33 (s, 1H), 4.62 (d, J=5.6 Hz, 2H), 3.81 (s, 3H), 3.73 (t, J=7.2 Hz, 2H), 3.04 (t, J=6.8 Hz, 2H). MS (APCI+) [M+H]+276.

Workup

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

Sources & evidence

ORD record
ord-72c4bdf021f74e1fbd53b37ac7d7140e
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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