Triphenylphosphine → HCID 58960248, compound

HRID 916459Notes

Reaction equation

HRID 916459 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:25][CH3:26])=[C:21]([OH:24])[CH:22]=2)[N:17]=[CH:16][N:15]=1.[C:27]([N:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][CH2:38]O)[CH2:32][CH2:31]1)(=[O:29])[CH3:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:27]([N:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][CH2:38][O:24][C:21]2[CH:22]=[C:23]3[C:18](=[CH:19][C:20]=2[O:25][CH3:26])[N:17]=[CH:16][N:15]=[C:14]3[Cl:13])[CH2:32][CH2:31]1)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 114467711-(4-(3-Hydroxypropyl)piperazin-1-yl)ethan-1-oneHCID 231324754-Chloro-7-methoxyquinazolin-6-ol

Product 1

HCID 58960248HCID 58960248, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (991 mg, 5.7 mmol) was added dropwise to a solution of 4-chloro-6-hydroxy-7-methoxyquinazoline (1 g, 4.75 mmol), 3-(4-acetylpiperazin-1-yl)propan-1-ol (972 mg, 5.22 mmol), (prepared as described for the starting material in Example 1 or Example 7), and triphenylphosphine (1.74 g, 6.65 mmol) in methylene chloride (25 ml). The mixture was stirred at ambient temperature for 2 hours. The solution was poured onto silica and eluted with methylene chloride, followed by methylene chloride/methanol (97/3 followed by 92/8). The fractions containing the expected product were combined and evaporated to give 6-[3-(4-acetylpiperazin-1-yl)propoxy]-4-chloro-7-methoxyquinazoline (1.3 g, 72%).

Workup

  1. custom(prepared
  2. additionThe solution was poured onto silica
  3. washeluted with methylene chloride
  4. additionThe fractions containing the expected product
  5. customevaporated

Sources & evidence

ORD record
ord-9cec12db23e0455d9ea804ecedb226f1
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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