Triphenylphosphine → 4-Chloro-6-methoxy-7-[3-(4-prop-2-yn-1-ylpiperazin-1-yl)propoxy]quinazoline

HRID 2068125ノート

反応式

HRID 2068125 の反応式
[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)[C:35]#[CH:36]>ClCCl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:45][CH2:44][CH2:43][N:40]3[CH2:39][CH2:38][N:37]([CH2:34][C:35]#[CH:36])[CH2:42][CH2:41]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 450998243-(4-Prop-2-YN-1-ylpiperazin-1-YL)propan-1-OLHCID 1357422514-Chloro-6-methoxyquinazolin-7-ol

生成物 1

HCID 589602354-Chloro-6-methoxy-7-[3-(4-prop-2-yn-1-ylpiperazin-1-yl)propoxy]quinazoline収率 77%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-Chloro-7-hydroxy-6-methoxyquinazoline (300 mg, 1.42 mmol), (prepared as described for the starting material in Example 4), was suspended in dichloromethane (15 ml). Triphenylphosphine (523 mg, 2 mmol) and 3-(4-prop-2-yn-1-ylpiperazin-1-yl)propan-1-ol (267 mg, 1.46 mmol) were added. Diisopropyl azadicarboxylate (340 μl, 1.71 mmol) was then added dropwise. The reaction mixture was stirred for 1.25 hours at ambient temperature and then loaded directly onto a silica column, and eluted with methylene chloride/methanol (90/8 followed by 90/10) to give 4-chloro-6-methoxy-7-[3-(4-prop-2-yn-1-ylpiperazin-1-yl)propoxy]quinazoline (409 mg, 77%).

後処理

  1. additionDiisopropyl azadicarboxylate (340 μl, 1.71 mmol) was then added dropwise
  2. washeluted with methylene chloride/methanol (90/8 followed by 90/10)

出典と根拠

ORDレコード
ord-4ac9bb9ccf034c2d9476593e58eafda8
出典データセット
uspto-grants-2012_10
特許番号
US08293902B2

反応ノート

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