Ethanol → (3-(((2-Amino-6-chloro-4-pyrimidinyl)amino)methyl)-3-oxetanyl)methanol

HRID 1421872Notes

Reaction equation

HRID 1421872 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][O:5][CH2:4]1.[NH2:9][C:10]1[N:15]=[C:14](Cl)[CH:13]=[C:12]([Cl:17])[N:11]=1.C(O)C>C(N(CC)CC)C>[NH2:9][C:10]1[N:15]=[C:14]([NH:1][CH2:2][C:3]2([CH2:7][OH:8])[CH2:6][O:5][CH2:4]2)[CH:13]=[C:12]([Cl:17])[N:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 655222-Amino-4,6-dichloropyrimidineHCID 18706850[3-(Aminomethyl)oxetan-3-yl]methanol

Product 1

HCID 385214(3-(((2-Amino-6-chloro-4-pyrimidinyl)amino)methyl)-3-oxetanyl)methanolYield 32.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 3-aminomethyl-3-hydroxymethyloxetane (1.17 g, 0.01 mol), 2-amino-4,6-dichloropyrimidine (1.64 g, 0.01 mol), ethanol (40 ml) and triethylamine (4 ml) was refluxed for one day. The solvent was distilled away under reduced pressure and ethyl acetate was added to the residue. The mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1, later 10:1) to give colorless prism crystals (0.8 g, 32.8%), m.p. 185-186° C. (acetone).

Workup

  1. temperaturewas refluxed for one day
  2. distillationThe solvent was distilled away under reduced pressure and ethyl acetate
  3. additionwas added to the residue
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-efe1ab6d86274af3afad69431d791d0c
Source dataset
uspto-grants-2000_06
Patent number
US06080750

Reaction notes

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