Morpholine → 7-(Morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Reaction equation

[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]=O)[N:6]2[N:5]=[CH:4][N:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[N:13]1([CH2:11][C:10]2[N:6]3[C:7]([C:2]([NH2:1])=[N:3][CH:4]=[N:5]3)=[CH:8][CH:9]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

Reactant 3

HCID 8083Morpholine

HCID 5049666Sodium triacetoxyborohydride

HCID 592319374-Aminopyrrolo(2,1-f)(1,2,4)triazine-7-carbaldehyde

Product 1

HCID 592319487-(Morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amineYield 20%

Procedure

To 4-aminopyrrolo[2,1-f][1,2,4]triazine-7-carbaldehyde(235 mg, 1.45 mmol) in 1,2-dichroloethane (5 ml) was added morpholine (0.25 ml, 2.9 mmol) and sodium triacetoxyborohydride (611 mg, 2.9 mmol). The reaction mixture was stirred at rt under N2 for 16 h. The reaction was quenched with saturated aq. sodium bicarbonate and followed by extraction with CH2Cl2. The organic was dried over Na2SO4, concentrated and purified via column chromatography (5:95 v/v CH3OH—CH2Cl2) to afford 66 mg of the title compound (yield 20%). 1H-NMR (DMSO-d6) δ 7.80 (s, 1H), 7.62 (br, 2H), 6.83 (d, J=4 Hz, 1H), 6.52 (d, J=4 Hz, 1H), 3.75 (s, 2H), 3.51(t, J=4 Hz, 4H), 2.37(t, J=4 Hz, 4H); MS [M+H]+=234; LCMS RT=1.00 min.