Ethylene Glycol → HCID 22036262, compound

HRID 991661Notes

Reaction equation

HRID 991661 reaction equation
O(C(C)(C)C)[K].[CH2:7]([OH:10])[CH2:8][OH:9].Br[C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1>C(Cl)Cl>[N:14]1[CH:13]=[C:12]([O:9][CH2:8][CH2:7][OH:10])[CH:17]=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 783445-BromopyrimidineHCID 178418922HCID 178418922, compound

Product 1

HCID 22036262HCID 22036262, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

KO-t-Bu (7.70 g, 68.6 mmol) was added to ethylene glycol (10.45 g, 168.4 mmol) under stirring. The mixture was gently heated in order to consume all KO-t-Bu. 5-Bromopyrimidine (8.45 g, 53.1 mmol) was added to the light brownish mixture. After 8 h of stirring at 130° C., CH2Cl2 (50 mL) was added to the brownish reaction mixture and two layers were formed. The CH2Cl2 layer was saved and the other layer was extracted with additional portions of CH2Cl2. The combined CH2Cl2 layers were concentrated in vacuo and the oily residue purified by column chromatography on silica gel using CHCl3/MeOH (9: 1) as eluent to give 0.45 g (6%) of the title product as an oil sufficiently pure for the next step. HRMS m/z calcd for C6H8N2O2 (M)+ 140.0586, found 140.0589.

Workup

  1. temperatureThe mixture was gently heated in order
  2. customto consume all KO-t-Bu
  3. stirringAfter 8 h of stirring at 130° C.
  4. customtwo layers were formed
  5. extractionthe other layer was extracted with additional portions of CH2Cl2
  6. concentrationThe combined CH2Cl2 layers were concentrated in vacuo
  7. customthe oily residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-37e82440f819427e8f361f77fe3a0e9f
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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