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1,1,3,3-Tetramethylguanidine → (Z)-methyl 2-(benzyloxycarbonylamino)-3-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)acrylate

HRID 2036838
ノート
印刷プレビュー

反応式

HRID 2036838 の反応式
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[N:10][C:11]([CH:17]=O)=[N:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:27]([O:34][C:35]([NH:37][CH:38](P(OC)(OC)=O)[C:39]([O:41][CH3:42])=[O:40])=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CN(C)C(=N)N(C)C>C1COCC1.C(OCC)(=O)C>[CH2:27]([O:34][C:35]([NH:37]/[C:38](=[CH:17]\[C:11]1[N:10]=[C:9]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:8]2[C:13](=[CH:14][CH:15]=[CH:16][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:12]=1)/[C:39]([O:41][CH3:42])=[O:40])=[O:36])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 664601,1,3,3-TetramethylguanidineHCID 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetateHCID 866706195-Phenyl-4-(pyridin-2-ylmethylamino)quinazoline-2-carbaldehyde

生成物 1

HCID 67055924(Z)-methyl 2-(benzyloxycarbonylamino)-3-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)acrylate収率 48%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-phenyl-4-(pyridin-2-ylmethylamino)quinazoline-2-carbaldehyde (0.9 g, 3 mmol) in THF (10 mL) was added methyl 2-benzyloxycarbonylamino-2(dimethoxyphosphinyl)acetate (0.96 g, 2.9 mmol) followed by tetramethyguanidine (0.66 mL. 5.3 mmol). The resulting solution was stirred at RT for 3 h. After this time, the reaction mixture was diluted with ethyl acetate, washed successively with water and brine, dried over Na2SO4, filtered then and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (30% ethyl acetate in hexane) to yield (Z)-methyl 2-(benzyloxycarbonylamino)-3-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)acrylate (0.7 g (48% yield). LCMS Method V: retention time 1.94 min; [M+1]=546.0.

後処理

  1. washwashed successively with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-88efaa75c19441e08844b0cf861be65b
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08575184B2

反応ノート

読み込み中…

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