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 925527Notes

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-a58666ac6880451d82a116ce00639539
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284316B2

Reaction notes

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