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1,2-Dichloroethane → Isopropyl-{4-methyl-6-[3-(4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrimidin-2-yl}-amine

HRID 2069425
ノート
印刷プレビュー

反応式

HRID 2069425 の反応式
[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[C:7]([CH3:14])[N:6]=1)([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.O[NH:30][C:31](=[NH:40])[C:32]1[CH:37]=[CH:36][C:35]([CH:38]=[CH2:39])=[CH:34][CH:33]=1>CN(C=O)C.O1CCOCC1.CCOC(C)=O>[CH:1]([NH:4][C:5]1[N:6]=[C:7]([CH3:14])[CH:8]=[C:9]([C:11]2[O:13][N:40]=[C:31]([C:32]3[CH:37]=[CH:36][C:35]([CH:38]=[CH2:39])=[CH:34][CH:33]=3)[N:30]=2)[N:10]=1)([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 669337152-(Isopropylamino)-6-methylpyrimidine-4-carboxylic acidHCID 178436434HCID 178436434、化合物

生成物 1

HCID 68509545Isopropyl-{4-methyl-6-[3-(4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrimidin-2-yl}-amine収率 81.1%

試薬・触媒・溶媒 3

HCID 6228
Dimethylformamide
溶媒
2 回
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

To a suspension of 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid (1.9 g, 11.8 mmol) in DMF (25 mL) is added HOBt (1.8 g, 13.4 mmol) followed by EDC (2.6 g, 13.4 mmol). The reaction mixture is stirred for 40 min until a clear solution is obtained and a solution of N-hydroxy-4-vinyl-benzamidine (2.09 g, 10.7 mmol) in DMF (20 mL) is added. After 2 h, EtOAc (320 mL) is added to the reaction mixture and the solution is then washed with sat. aq. NaHCO3 (3×100 mL), with brine, dried over MgSO4, filtered and evaporated to give a red oil. The oil is dissolved in dioxane (50 mL) and the solution is heated to 95° C. for 2 h. The reaction mixture is evaporated and purification by CC on silica gel affords the title compound as a yellow oil (2.79 g); LC-MS: tR=1.12; [M+H]+=321.95.

後処理

  1. customis obtained
  2. waitAfter 2 h
  3. washthe solution is then washed with sat. aq. NaHCO3 (3×100 mL), with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a red oil
  8. customThe reaction mixture is evaporated
  9. custompurification by CC on silica gel

出典と根拠

ORDレコード
ord-fbe9e60c8874461ea8981517758cc647
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299086B2

反応ノート

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