Triphenylphosphine → HCID 86597574, compound

HRID 1785124Notes

Reaction equation

HRID 1785124 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([OH:28])=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[CH:18][N:17]=1.[F:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][CH2:40]O)[CH2:34][CH2:33]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C1COCC1.ClCCl>[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:40][CH2:39][CH2:38][N:35]3[CH2:34][CH2:33][N:32]([CH2:31][CH2:30][F:29])[CH2:37][CH2:36]3)=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[CH:18][N:17]=1

Participants

8

Reactant 5

HCID 11776Triphenylphosphine2×HCID 5363146Diisopropyl azodicarboxylateHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 451157673-[4-(2-Fluoroethyl)piperazin-1-YL]propan-1-OLHCID 1357422514-Chloro-6-methoxyquinazolin-7-ol

Product 1

HCID 86597574HCID 86597574, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazodicarboxylate (921 mg, 4.56 mmol) was added portionwise, at room temperature, to a stirred suspension of 4-chloro-6-methoxyquinazolin-7-ol (800 mg, 3.80 mmol), 3-[4-(2-fluoroethyl)piperazin-1-yl]propan-1-ol (794 mg, 4.18 mmol) and triphenylphosphine (1.4 g, 5.34 mmol) in THF (20 ml). The reaction was stirred 1 hr. before adding triphenylphosphine (1.4 g), di-tert-butylazodicarboxylate (1.05 g, 4.56 mmol) and dichloromethane (10 ml). The reaction was stirred for a further 1 hr. then evaporated and purified by column chromatography on silica using increasing concentrations of methanol in dichloromethane as eluent then on alumina (neutral) using 10% methanol in dichloromethane as eluent to give 4chloro-7-{3-[4-(2-fluoroethyl)piperazin-1-yl]propoxy}-6-methoxyquinazoline (696 mg, 48%) as a colourless solid; NMR Spectrum:(CDCl3) 2.13 (quintet, 2H), 2.55 (m, 10H), 2.67 & 2.76 (dt, 2), 4.06 (s, 3H), 4.30 (t, 2H), 4.53 & 4.64 (dt, 2H), 7.36 (s, 1H), 7.38 (s, 1H), 8.86 (s, 1H).

Workup

  1. stirringThe reaction was stirred for a further 1 hr
  2. customthen evaporated
  3. custompurified by column chromatography on silica using
  4. temperatureincreasing concentrations of methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-319d7e7bc5a547a9ad5d7b42063f980a
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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