Diethyl (ethoxymethylene)malonate → HCID 178469753, compound

HRID 1584860Notes

Reaction equation

C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[C:16]1([CH2:22][C:23]([NH2:25])=[NH:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:22]([C:23]1[N:25]=[C:11]([OH:13])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonate

HCID 27787Benzeneethanimidamide

Product 1

HCID 178469753HCID 178469753, compoundYield 40%

Procedure

The title compound was prepared by (a) reaction of diethyl ethoxymethylenemalonate (11 g, 52 mmol) with phenylacetamidine (8 g, 60 mmol) to afford 40% of ethyl 2-benzyl-4-hydroxypyrimidine-5-carboxylate in analogy to Example 15, (b) reaction of 2-benzyl-4-hydroxypyrimidine-5-carboxylate (3 g, 12 mmol) with POCl3 (18 g, 116 mmol) to afford 45% of 2-benzyl-4-chloropyrimidine-5-carboxylate in analogy to Example 7, (c) reaction of 2-benzyl-4-chloropyrimidine-5-carboxylate (1.5 g, 5.5 mmol) with hydrazine (0.5 g, 16 mmol) to afford 75% of 2-benzyl-4-hydrazinopyrinmidine-5-carboxylate in analogy to Example 18, (d) reaction of ethyl 2-benzyl-4-hydrazinopyrimidine-5-carboxylate (1 g, 3.5 mmol) with citraconic anhydride (1 g, 11 mmol), in analogy to Example 21, to afford 70% (0.9 g) of the title compound; m.p. 117-118° C.

Sources & evidence

ORD record: ord-4b65951fa91641beb3fdaff8777d6fc8
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935966

Reaction notes

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