Diisopropylethylamine → HCID 19917925, compound

HRID 1755856Notes

Reaction equation

HRID 1755856 reaction equation
[CH:1]([CH:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[C:4](OC)=O)=[O:2].Cl.[CH:19]([NH2:21])=[NH:20].C(N(C(C)C)C(C)C)C>C(O)C>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([C:3]2[C:1](=[O:2])[NH:21][CH:19]=[N:20][CH:4]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 19917879HCID 19917879, compound

Product 1

HCID 19917925HCID 19917925, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-formyl-2-(3,4-dimethoxyphenyl)acetate (7.2 g) (30 mmol), 4.8 g (60 mmol) of formamidine hydrochloride and 7.74 g (60 mmol) of N-ethyldiisopropylamine (Hunig base) are stirred in 60 ml of ethanol for 55 hours at 50° C. and subsequently concentrated in a vacuum. The residue is washed several times with diethyl ether and then crystallized using ethanol/diethyl ether. The yellowish product is filtered off under suction, washed with ethanol/diethyl ether and dried in a high vacuum at room temperature. There are obtained 1.6 g of 5-(3,4-dimethoxyphenyl)-4(3H)-pyrimidinone of m.p. 205°-206° C.

Workup

  1. concentrationsubsequently concentrated in a vacuum
  2. washThe residue is washed several times with diethyl ether
  3. customcrystallized
  4. filtrationThe yellowish product is filtered off under suction
  5. washwashed with ethanol/diethyl ether
  6. customdried in a high vacuum at room temperature

Sources & evidence

ORD record
ord-04e1b502e5a845e3b41d9f520cf2a2f6
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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