Ammonium Chloride → 3-Propyl-6-propylthio-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

HRID 373233Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:21]([S:22][CH2:23][CH2:24][CH3:25])=[CH:20][C:19](=[O:26])[N:18]([CH2:27][CH2:28][CH3:29])[C:17]2=[O:30])=[CH:11][CH:10]=1)#[N:2].[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+]>CN(C)C=O.C(Cl)Cl>[CH2:27]([N:18]1[C:19](=[O:26])[CH:20]=[C:21]([S:22][CH2:23][CH2:24][CH3:25])[N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]3[NH:33][N:32]=[N:31][N:2]=3)=[CH:14][CH:13]=2)[C:17]1=[O:30])[CH2:28][CH3:29]

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 1-(2'-cyanobiphenyl-4-yl)methyl-3-propyl-6-propylthiopyrimidine-2,4(1H,3H)-dione (0.77 g), sodium azide (1.8 g) and ammonium chloride (1.48 g) in dimethylformamide (10 ml) was heated at 115° C. for 84 hours. The reaction mixture was diluted with methylene chloride and then the precipitate was filtered. The filtrate was concentrated to dryness in vacuo. The resulting residue was extracted with methylene chloride water. The organic layer was washed with water, dried, and evaporated to dryness. The resulting residue was purified by column chromatography on silica gel to give yellow amorphous powders (0.41 g, 46%).

Workup

filtrationthe precipitate was filtered
concentrationThe filtrate was concentrated to dryness in vacuo
extractionThe resulting residue was extracted with methylene chloride water
washThe organic layer was washed with water
customdried
customevaporated to dryness
customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-8ff225c01e2240aba447f84762656c28
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162326

Reaction notes

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