Ethylamine → HCID 178463437, compound

HRID 2290619Notes

Reaction equation

HRID 2290619 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([OH:9])[C:3]=1[CH:10]([CH3:12])[CH3:11].[CH2:13]([NH2:15])[CH3:14]>>[CH2:13]([NH:15][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([OH:9])[C:3]=1[CH:10]([CH3:12])[CH3:11])[CH3:14]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 178433447HCID 178433447, compound

Product 1

HCID 178463437HCID 178463437, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 3.00 g (16.1 mmol) of 6-Chloro-2-methyl-5-(1-methylethyl)-4-pyrimidinol and 10.4 mL (7.24 g, 161 mmol, 10 equiv.) of ethylamine as a 70% w/w aqueous solution was sealed in a glass flask, heated at 90° C. for 5 days, and then cooled to 23° C. The mixture was concentrated in vacuo and purified by flash chromatography (silica gel, 50 mm column, 500 mL 4:1 EtOAc:hexane then EtOAc as eluent, mixed fractions rechromatographed) to provide 1.32 g (7.01 mmol, 44%) of recovered starting material and, after recrystallization from EtOAc, 1.70 g (8.70 mmol, 54%) of analytically pure product as a dense white crystalline solid, m.p. 179.5°-180° C.

Workup

  1. customwas sealed in a glass flask
  2. temperaturecooled to 23° C
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by flash chromatography (silica gel, 50 mm column, 500 mL 4:1 EtOAc
  5. additionhexane then EtOAc as eluent, mixed fractions
  6. customrechromatographed)
  7. customto provide 1.32 g (7.01 mmol, 44%)
  8. customof recovered
  9. customafter recrystallization from EtOAc, 1.70 g (8.70 mmol, 54%) of analytically pure product as a dense white crystalline solid, m.p. 179.5°-180° C.

Sources & evidence

ORD record
ord-9476449bdad048bca7e10fbc5396e90e
Source dataset
uspto-grants-1986_10
Patent number
US04617393

Reaction notes

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