Triphenylphosphine → HCID 58960221, compound

HRID 916439Notes

Reaction equation

HRID 916439 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:34]([N:37]1[CH2:42][CH2:41][N:40]([CH2:43][CH2:44][CH2:45]O)[CH2:39][CH2:38]1)[CH:35]=[CH2:36].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[CH2:34]([N:37]1[CH2:38][CH2:39][N:40]([CH2:43][CH2:44][CH2:45][O:14][C:8]2[CH:7]=[C:6]3[C:11]([C:2]([Cl:1])=[N:3][CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])[CH2:41][CH2:42]1)[CH:35]=[CH2:36]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 15572524HCID 15572524, compoundHCID 1357422514-Chloro-6-methoxyquinazolin-7-ol

Product 1

HCID 58960221HCID 58960221, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chloro-7-hydroxy-6-methoxyquinazoline (300 mg, 1.43 mmol), (prepared as described for the starting material in Example 4), in methylene chloride (15 ml) was added triphenylphosphine (522 mg, 2.0 mmol), 3-(4-allylpiperazin-1-yl)propan-1-ol (288 mg, 1.57 mmol), (DE 2755707), and diisopropyl azodicarboxylate (336 μl, 1.71 mmol) and the mixture stirred at ambient temperature for 2 hours. The crude reaction mixture was loaded directly onto a silica chromatography column and eluted with methylene chloride/methanol (95/5). The volatile solvents were removed under vacuum to give 7-[3-(4-allylpiperazin-1-yl)propoxy]-4-chloro-6-methoxyquinazoline as an oil which crystallised on standing (480 mg, 89%).

Workup

  1. custom(prepared
  2. customThe crude reaction mixture
  3. washeluted with methylene chloride/methanol (95/5)
  4. customThe volatile solvents were removed under vacuum

Sources & evidence

ORD record
ord-7aa27fb766f142dcb6f688e13c1256a0
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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