Sodium hydride → HCID 385279, compound

HRID 1421873Notes

Reaction equation

HRID 1421873 reaction equation
[H-].[Na+].O[CH:4]([CH:6]1[CH2:9][CH2:8][CH2:7]1)[OH:5].[NH2:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[C:13]([Cl:18])[N:12]=1.[O:19]1CCOC[CH2:20]1>>[NH2:10][C:11]1[N:16]=[C:15]([O:5][CH2:4][C:6]2([CH2:20][OH:19])[CH2:9][CH2:8][CH2:7]2)[CH:14]=[C:13]([Cl:18])[N:12]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 312751,4-Dioxane2×HCID 655222-Amino-4,6-dichloropyrimidineHCID 17797766HCID 17797766, compound

Product 1

HCID 385279HCID 385279, compoundYield 50.8%

Conditions

Temperature
65 °C

Procedure

60% Sodium hydride (0.4 g, 0.01 mol) was suspended in dry dioxane (40 ml) and dihydroxymethylcyclobutane (1.16 g, 0.01 mol) dissolved in dry dioxane (40 ml) was dropwise added thereto. The mixture was stirred at 60-70° C. for 30 minutes, and 2-amino-4,6-dichloropyrimidine (1.64 g, 0.01 mol) was added. The mixture was refluxed for 3 hours, and filtrated. The solvent in the filtrate was distilled away under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=50:1) to give white crystals (1.24 g, 50.8%), m.p. 125-127° C. (acetone).

Workup

  1. additionwas dropwise added
  2. temperatureThe mixture was refluxed for 3 hours
  3. filtrationfiltrated
  4. distillationThe solvent in the filtrate was distilled away under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-febe5ae2d7c14114a4b2a1d8060a7cc7
Source dataset
uspto-grants-2000_06
Patent number
US06080750

Reaction notes

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