Tetrahydrofuran → HCID 67340407, compound

HRID 1668993Notes

Reaction equation

HRID 1668993 reaction equation
[CH3:1][C:2]1[C:3]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[C:27]([NH:32][CH3:33])[N:26]=[CH:25]3)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13]1[CH:14]=[C:15](CC=O)[CH:16]=[CH:17][CH:18]=1)=[N:7][N:6]=[CH:5]2.[CH2:34]1[CH2:38][O:37]CC1.[CH3:39][Mg]Br.C1(C)C=CC=CC=1.O1CCCC1>O>[CH3:1][C:2]1[C:3]([C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[C:27]([NH:32][CH3:33])[N:26]=[CH:25]3)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13]1[CH:14]=[C:15]([C:38]([OH:37])([CH3:34])[CH3:39])[CH:16]=[CH:17][CH:18]=1)=[N:7][N:6]=[CH:5]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 22635083Tetrahydrofuran tolueneHCID 86614222HCID 86614222, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67340407HCID 67340407, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(3-(6-methyl-5-(2-(methylamino)quinazolin-6-yl)phthalazin-1-ylamino)phenyl)ethanone (0.056 g, 0.13 mmol)n THF (2.0 ml), charged to a 50 mL round bottom, methylmagnesium bromide, 1.4 m solution in toluene/tetrahydrofuran (75:25) (0.19 ml, 0.27 mmol) was added at 0° C. The reaction mixture was stirred for 2 h. The reaction mixture was diluted with water and extracted with DCM. The combined organics were washed with brine, dried over magnesium sulfate and concentrated under vacuum. The resulting residue was loaded on to silica and purified by column Chromatography. (ISCO 12.0 g, 1-7% MeOH in DCM, 25 min.) to give 2-(3-(6-methyl-5-(2-(methylamino)quinazolin-6-yl)phthalazin-1-ylamino)phenyl)propan-2-ol. MS (M+H)+ 451.

Workup

  1. extractionextracted with DCM
  2. washThe combined organics were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. custompurified by column Chromatography

Sources & evidence

ORD record
ord-2309e024b26f4293a39e26fb81dbf461
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Reaction notes

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