Methyl acetoacetate → HCID 136393284, compound

HRID 1868450Notes

Reaction equation

HRID 1868450 reaction equation
[NH:1]1[C:5]([NH2:6])=[N:4][C:3]([NH2:7])=[N:2]1.O=[C:9]([CH3:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12].[Cl:16][C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[CH:19]=O.N1CCCCC1>C1COCC1.CCCCCCC>[NH2:6][C:5]1[N:4]=[C:3]2[NH:7][C:9]([CH3:15])=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:19]([C:18]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:17]=3[Cl:16])[N:2]2[N:1]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 8082PiperidineHCID 134042,4-DichlorobenzaldehydeHCID 150783,5-Diamino-1,2,4-triazole

Product 1

HCID 136393284HCID 136393284, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 1H-1,2,4-triazole-3,5-diamine (1.0 g, 10.1 mmol), methyl 3-oxobutanoate (1.17 g, 10.1 mmol), and 2,4-dichlorobenzaldehyde (1.35 g, 10.1 mmol) in THF (30 mL) and heptane (8 mL) was added piperidine (30 mg, 0.3 mmol) and the reaction was heated to 70° C. for 2 days. The reaction was concentrated to afford crude methyl 2-amino-7-(2,4-dichlorophenyl)-5-methyl-4,7-dihydro-[1,2,4]-triazolo[1,5-a]pyrimidine-6-carboxylate as a light yellow solid.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-602fa7dc02fc47369f121972f3e5f251
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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