1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-Benzyl-1H-pyrazole-4-carboxylic acid (6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide

HRID 535978Notes

Reaction equation

[NH2:1][C:2]1[C:3](=[O:13])[N:4]([CH2:10][CH2:11][CH3:12])[C:5](=[O:9])[NH:6][C:7]=1[NH2:8].[CH2:14]([N:21]1[CH:25]=[C:24]([C:26](O)=[O:27])[CH:23]=[N:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.Cl>CO>[NH2:8][C:7]1[NH:6][C:5](=[O:9])[N:4]([CH2:10][CH2:11][CH3:12])[C:3](=[O:13])[C:2]=1[NH:1][C:26]([C:24]1[CH:23]=[N:22][N:21]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:25]=1)=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 5,6-diamino-3-propyl-1H-pyrimidine-2,4-dione (1.6 g, 8.55 mmol), 1-benzyl-1H-pyrazole-4-carboxylic acid (1.75 g, 8.65 mmol) in methanol (10 ml) were cooled to 0° C. and added EDCI.HCl (2.32 g, 12.11 mmol). The reaction mixture was stirred at 25° C. for 20 hours and the solvents were removed under reduced pressure. To this residue water (10 ml) was added and the precipitate was filtered off, and was washed sequentially with cold water (20 ml) and DCM (25 ml) to obtain 1-Benzyl-1H-pyrazole-4-carboxylic acid (6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (1.5 g, 47%) as a pale yellow solid.

Workup

customthe solvents were removed under reduced pressure
additionTo this residue water (10 ml) was added
filtrationthe precipitate was filtered off
washwas washed sequentially with cold water (20 ml) and DCM (25 ml)

Sources & evidence

ORD record: ord-f2d320e766924a928bf6fe1c1bb46c20
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859566B2

Reaction notes

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