Triphenylphosphine → 6-(3-Methanesulfonyl-propoxy)-5-methyl-4-phenoxypyrrolo[2,1-f][1,2,4]triazine

HRID 914795Notes

Reaction equation

HRID 914795 reaction equation
[O:1]([C:8]1[C:13]2=[C:14]([CH3:18])[C:15]([OH:17])=[CH:16][N:12]2[N:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][S:20]([CH2:23][CH2:24][CH2:25]O)(=[O:22])=[O:21].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:19][S:20]([CH2:23][CH2:24][CH2:25][O:17][C:15]1[C:14]([CH3:18])=[C:13]2[N:12]([CH:16]=1)[N:11]=[CH:10][N:9]=[C:8]2[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2004243-(Methylsulfonyl)-1-propanolHCID 5462977Diethyl azodicarboxylateHCID 219458735-Methyl-4-phenoxypyrrolo[2,1-f][1,2,4]triazin-6-ol

Product 1

HCID 225088806-(3-Methanesulfonyl-propoxy)-5-methyl-4-phenoxypyrrolo[2,1-f][1,2,4]triazineYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-phenoxy-5-methyl-6-hydroxypyrrolo-[2,1-f][1,2,4]triazine (1.0 g, 4.15 mmol, as prepared in WO 00/71129, which is hereby incorporated by reference), 3-methanesulfonylpropan-1-ol (1.15 g, 8.3 mmol) and PPh3 (2.17 g, 8.3 mmol) in THF (12 mL) at 0° C., was added DEAD (1.42 g, 8.3 mmol). The mixture was stirred at RT for 1 h. The solvent was removed in vacuo. The residue was dissolved in dichloromethane, washed with brine and dried (Na2SO4). The volatiles were removed and the solid obtained was triturated with dichloromethane to afford 6-(3-methanesulfonylpropoxy)-5-methyl-4-phenoxypyrrolo[2,1-f][1,2,4]triazine as a white solid (1.1 g, 73% yield). MS: (M+H)+=362.

Workup

  1. customat 0° C.
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe volatiles were removed
  7. customthe solid obtained
  8. customwas triturated with dichloromethane

Sources & evidence

ORD record
ord-10da48ebc7b74c22a6396f03e221ec24
Source dataset
uspto-grants-2007_09
Patent number
US07265113B2

Reaction notes

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