Triphenylphosphine → 5-Methyl-4-phenoxy-6-(3-piperidin-1-yl-propoxy)-pyrrolo[2,1-f][1,2,4]triazine

HRID 914791Notes

Reaction equation

[CH3:1][C:2]1[C:3]([OH:18])=[CH:4][N:5]2[C:10]=1[C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[N:8][CH:7]=[N:6]2.[N:19]1([CH2:25][CH2:26][CH2:27]O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:1][C:2]1[C:3]([O:18][CH2:27][CH2:26][CH2:25][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][N:5]2[C:10]=1[C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[N:8][CH:7]=[N:6]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 5-methyl-4-phenoxypyrrolo[2,1-f][1,2,4]triazin-6-ol (1.47 g, 6.1 mmol, for preparation see WO 0071129), 1-piperidinepropanol (1.74 g, 12.2 mmol) and triphenylphosphine (3.2 g, 12.2 mmol) in tetrahydrofuran (20 mL) at 0° C. under argon, was added DEAD (1.9 mL, 12.2 mmol). The resulting mixture was stirred at 0° C. for 30 min, and then at RT for 1 hr. The volatiles were removed in vacuo. The residue was purified by silica gel flash column chromatography using 5% (2M NH3 in MeOH)/20% ethyl acetate /CH2Cl2 to afford the desired product as beige solid (1.6 g, 72% yield). MS: (M+H)+=367.

Workup

waitat RT for 1 hr
customThe volatiles were removed in vacuo
customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record: ord-1c2d2f014f234ceaa1f62707beba4410
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265113B2

Reaction notes

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