Formaldehyde → 2-(Pyrimidin-4-yl)ethan-1-ol

HRID 854347Notes

Reaction equation

HRID 854347 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[CH2:8]=[O:9]>CCOCC>[OH:9][CH2:8][CH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 189224-Methylpyrimidine

Product 1

HCID 154753442-(Pyrimidin-4-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-methylpyrimidine (10 g, 106 mmol) and para-formaldehyde (3 g) was stirred in a 50 mL sealed capacity pressure vessel at 165° C. for 3.5 hours. After cooling, ether was added and the solvents evaporated to afford an oil. This was purified by silica column chromatography using a Flashmaster system, eluting with dichloromethane, then chloroform, ether, and finally ethyl acetate. The ethyl acetate fractions were evaporated to afford the title compound as an oil.

Workup

  1. customsealed capacity pressure vessel at 165° C. for 3.5 hours
  2. temperatureAfter cooling
  3. customthe solvents evaporated
  4. customto afford an oil
  5. customThis was purified by silica column chromatography
  6. washeluting with dichloromethane
  7. customThe ethyl acetate fractions were evaporated

Sources & evidence

ORD record
ord-24aa06d178004867a09c8cf2f8c473d2
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

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