Formaldehyde → 5-(Furan-3-yl)-8-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[4,3-a]pyrazine

HRID 1045711Notes

Reaction equation

Cl.[O:2]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]3[CH:13]=[N:14][N:15]=[C:11]3[C:10]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[N:9][CH:8]=2)=[CH:3]1.C=O.Cl[CH2:25]Cl.C([BH3-])#N.[Na+]>CO>[O:2]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]3[CH:13]=[N:14][N:15]=[C:11]3[C:10]([N:16]3[CH2:17][CH2:18][N:19]([CH3:25])[CH2:20][CH2:21]3)=[N:9][CH:8]=2)=[CH:3]1

Participants

Conditions

Temperature: 20 °C

Procedure

A 50 mL round bottom flask was charged with 5-(furan-3-yl)-8-(piperazin-1-yl)-[1,2,4]triazolo[4,3-a]pyrazine HCl salt (350 mg, 1.14 mmol), 40% aqueous formaldehyde (20 mL), dichloromethane (20 mL), methanol (20 mL) and sodium cyanoborohydride (245 mg, 3.90 mmol) at 0° C. The resulting mixture was stirred at 20° C. overnight. It was then concentrated in vacuo and the residue was extracted with dichloromethane. The organic layer was washed with brine (10 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was re-crystallized from a 1/5 (v/v) dichloromethane/ethyl ether, to afford 0.16 g (49%) of the product as a yellow solid. 1H NMR (300 MHz, CDCl3) δ: 8.83 (s, 1H), 7.76 (dd, J=1.5, 0.9 Hz, 1H), 7.62 (dd, J=1.8, 1.5 Hz, 1H), 7.36 (s, 1H), 6.68 (dd, J=1.8, 0.9 Hz, 1H), 4.41 (br, 4H), 2.59 (t, J=5.1 Hz, 4H), 2.36 (s, 3H). MS m/z: 285 (M+H+).

Workup

concentrationIt was then concentrated in vacuo
extractionthe residue was extracted with dichloromethane
washThe organic layer was washed with brine (10 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe crude product was re-crystallized from a 1/5 (v/v) dichloromethane/ethyl ether

Sources & evidence

ORD record: ord-8c715ad0d14443ceae3ea843dfd6a821
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569300B2

Reaction notes

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