Ethanolamine → 2-{[2,6-Di(pyrrolidin-1-yl)pyrimidin-4-yl]amino}ethan-1-ol

HRID 482316Notes

Reaction equation

HRID 482316 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]=[C:4]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:3]=1.[CH2:18]([CH2:20][NH2:21])[OH:19]>O>[N:13]1([C:4]2[N:3]=[C:2]([NH:21][CH2:20][CH2:18][OH:19])[CH:7]=[C:6]([N:8]3[CH2:12][CH2:11][CH2:10][CH2:9]3)[N:5]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 7036994-Chloro-2,6-di(pyrrolidin-1-yl)pyrimidine

Product 1

HCID 155216142-{[2,6-Di(pyrrolidin-1-yl)pyrimidin-4-yl]amino}ethan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-2,6-di-1-pyrrolidinyl-pyrimidine (II, J. Med. Chem., 33, 1145 (1990), 300 g) in ethanolamine (1000 mL) is heated at 140° for 66 hr. The reaction mixture is cooled, diluted with water (1700 mL) and the product is isolated by filtration, to give the title compound, mp=150.5-151.50°; NMR (CDCl3) 6.55, 4.83, 4.75, 3.75-3.72, 3.54-3.38 and 1.93-1.85 δ.

Workup

  1. temperatureis heated at 140° for 66 hr
  2. temperatureThe reaction mixture is cooled
  3. customthe product is isolated by filtration

Sources & evidence

ORD record
ord-de97ccd88db84a5b8777b0f7dfacd788
Source dataset
uspto-grants-1998_08
Patent number
US05795986

Reaction notes

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