1-Butanol → HCID 59852864, compound

HRID 2237161Notes

Reaction equation

HRID 2237161 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.Cl.[CH3:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[C:13]=1[CH2:14][NH2:15].CCN(C(C)C)C(C)C.CCCCO>O>[CH3:23][O:22][C:16]1[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=[C:12]([O:11][CH3:10])[C:13]=1[CH2:14][NH:15][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 162119141-(2,4,6-Trimethoxyphenyl)methanamine--hydrogen chloride (1/1)

Product 1

HCID 59852864HCID 59852864, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4,6-dichloropyrimidine (Aldrich, 1.48 g, 10.0 mmol), 2,4,6-trimethoxybenzylamine hydrochloride (2.33 g, 10.0 mmol), DIPEA (4.8 mL, 27.7 mmol), and n-BuOH (50 mL) was heated at 100° C. for 2 h. The mixture was cooled, diluted with water (200 mL) and the precipitated product was collected by vacuum filtration on a Büchner funnel. The product was washed with cold water, ether, and vacuum dried to give an off-white solid (2.8 g, 90%). 1H NMR (DMSO-d6) δ 8.28 (s, 1H), 7.38 (s, 1H), 6.49 (s, 1H), 6.25 (s, 2H), 4.34 (s, 2H), 3.77 (s, 9H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitated product was collected by vacuum filtration on a Büchner funnel
  3. washThe product was washed with cold water, ether, and vacuum
  4. customdried

Sources & evidence

ORD record
ord-c753120b4a4c45498f1cdbe047272477
Source dataset
uspto-grants-2010_05
Patent number
US07714138B2

Reaction notes

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