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

HRID 1099250Notes

Reaction equation

HRID 1099250 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

4

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 59231937939967-94-9

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.

Workup

  1. customThe reaction was quenched with saturated aq. sodium bicarbonate
  2. extractionfollowed by extraction with CH2Cl2
  3. dry with materialThe organic was dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified via column chromatography (5:95 v/v CH3OH—CH2Cl2)

Sources & evidence

ORD record
ord-0622a17c2f0844f291e5f18a5616a60b
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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