Sodium Bicarbonate → (rac)-7-(4-Cyanophenyl)-2-(methoxymethyl)-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile

HRID 2200923Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[N:8]=[C:7]([NH2:9])[NH:6][N:5]=1.[C:10]([C:12]([C:22](=O)[CH3:23])=[CH:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)#[N:11].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([CH:13]2[N:6]3[N:5]=[C:4]([CH2:3][O:2][CH3:1])[N:8]=[C:7]3[NH:9][C:22]([CH3:23])=[C:12]2[C:10]#[N:11])=[CH:15][CH:16]=1)#[N:19]

Participants

Conditions

Temperature: 55 °C

Procedure

Under an atmosphere of argon, 3-(methoxymethyl)-1H-1,2,4-triazole-5-amine (244 mg, 1.9 mmol) and 4-(2-cyano-3-oxobut-1-en-1-yl)benzonitrile (300 mg, 1.5 mmol, 0.8 eq.) were dissolved in DMF (3 ml), and solid sodium bicarbonate (803 mg, 9.6 mmol, 5 eq.) was added. The mixture was stirred at 55° C. for 12 h. The mixture was then filtered, and the DMF from the filtrate was distilled off under reduced pressure. The residue was acidified with 1 N hydrochloric acid and then purified by preparative HPLC (Kromasil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). The product was obtained as a solid (38.2 mg, 80% pure, 7% of theory).

Workup

filtrationThe mixture was then filtered
distillationthe DMF from the filtrate was distilled off under reduced pressure
custompurified by preparative HPLC (Kromasil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
customThe product was obtained as a solid (38.2 mg, 80% pure, 7% of theory)

Sources & evidence

ORD record: ord-f7944d3bb7714882b22a39fa9eea06fd
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359362B2

Reaction notes

Loading…