Methanol → HCID 20208136, compound

HRID 542387Notes

Reaction equation

HRID 542387 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[N:5]=[CH:4][N:3]=1.[CH3:16][OH:17]>[Na]>[CH2:12]([N:11]([CH2:14][CH3:15])[C:6]1[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([O:17][CH3:16])[N:3]=[CH:4][N:5]=1)[CH3:13]

Participants

4

Reactant 2

HCID 887Methanol2×HCID 234772686-Chloro-N,N-diethyl-5-nitro-4-pyrimidinamine

Product 1

HCID 20208136HCID 20208136, compound

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Procedure

In a sulphonation flask are dissolved 17.25 g sodium metal in 1000 ml absolute CH3OH. The reaction mixture is cooled to ambient temperature and then a solution of 116 g 4 -chloro-6-diethylamino-5-nitropyrimidine in 500 ml absolute CH3OH is added dropwise thereto. The reaction temperature rises from 22° to 32°. The reaction mixture is then heated for one hour under reflux. The reaction mixture is cooled and concentrated. The residue is taken up in diethylether, washed with water, the organic phase is partitioned off and dried over Na2SO4, concentrated, chromatographed on a silica gel column (elution with diethylether/hexane 1:10) to give a yellow, clear oil (4-diethylamino-6-methoxy-5-nitropyrimidine), Rf=0.3 in ether/hexane 1:3.

Workup

  1. customrises from 22° to 32°
  2. temperatureThe reaction mixture is then heated for one hour
  3. temperatureunder reflux
  4. temperatureThe reaction mixture is cooled
  5. concentrationconcentrated
  6. washwashed with water
  7. customthe organic phase is partitioned off
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customchromatographed on a silica gel column (elution with diethylether/hexane 1:10)

Sources & evidence

ORD record
ord-18ecfd1a3b0f438a821f7a61920dd8b8
Source dataset
uspto-grants-1987_04
Patent number
US04657579

Reaction notes

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