Diethyl (ethoxymethylene)malonate → HCID 178469783, compound
Reaction equation
C(O[C:4](=[O:15])[C:5](=[CH:11]OCC)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.Cl.[C:17]([NH2:20])(=[NH:19])[CH3:18]>>[CH3:18][C:17]1[N:20]=[C:4]([OH:15])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][N:19]=1Participants
Procedure
The title compound was prepared by (a) reaction of diethylethoxymethylenemalonate (6 g, 28 mmol) with acetamidine hydrochloride (3 g, 31 mmol) to afford 67% of ethyl 2-methyl-4-hydroxypyrimidine-5-carboxylate in analogy to Example 15, (b) reaction of ethyl 2-methyl-4-hydroxypyrimidine-5-carboxylate (2.8 g, 15 mmol) with POCl3 (46 g, 300 mmol) to afford 28% of ethyl 4-chloro-2-methylpyrimidine-5-carboxylate, (c) reaction of ethyl 4-chloro-2-methylpyrimidine-5-carboxylate (0.25 g, 1.25 mmol) with hydrazine (0.2 g, 6.3 mmol) to afford 96% of 4-hydrazino-2-methylpyrimidine-5-carboxylate in analogy to Example 18, (d) reaction of 4-hydrazino-2-methylpyrimidine-5-carboxylate (0.24 g, 1.2 mmol) with citraconic anhydride (0.16 g, 1.44 mmol) to afford 70% (0.24 g) of the title compound (m.p. 98-99° C.) in analogy to Example 21.
Sources & evidence
- ORD record
- ord-f14967b3a94d41cf81ea89fbb3c11765
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05935966
Reaction notes
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