Triphenylphosphine → Isopropyl-[6-methoxy-7-(4-methylsulphanylbutoxy)quinazolin-4-yl]amine

HRID 249983Notes

Reaction equation

HRID 249983 reaction equation
[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1CCN(C(/N=N/C(N2CCCCC2)=O)=O)CC1.[CH3:55][S:56][CH2:57][CH2:58][CH2:59][CH2:60]O>C(Cl)Cl.O>[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH2:60][CH2:59][CH2:58][CH2:57][S:56][CH3:55])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5197934-(Methylthio)butanolHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 1358608004-(Isopropylamino)-6-methoxyquinazolin-7-ol

Product 1

HCID 57788016Isopropyl-[6-methoxy-7-(4-methylsulphanylbutoxy)quinazolin-4-yl]amineYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-(Isopropylamino)-6-methoxyquinazolin-7-ol (380 mg, 1.63 mmol) is dissolved in methylene chloride (10 ml) under an argon atmosphere, treated with triphenylphosphine (641 mg, 2.44 mmol), azodicarboxylic acid dipiperidide (617 mg, 2.44 mmol) and 4-(methylthio)butan-1-ol (235 mg, 1.96 mmol) and stirred at room temperature for 20 hours. The batch is diluted with methylene chloride and water, and the organic phase is separated off and concentrated. The desired product is obtained after chromatography by means of preparative HPLC in 43% yield (258 mg).

Workup

  1. customthe organic phase is separated off
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8d72008b3a72479bb67a19d9f37e3056
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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