Tetrahydrofuran → HCID 86649314、化合物

HRID 1042294ノート

反応式

HRID 1042294 の反応式
F[C:2]1[C:7]([C:8]2[N:16]=[CH:15][N:14]=[C:13]3[C:9]=2[N:10]=[CH:11][N:12]3[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[CH:6][CH:5]=[CH:4][N:3]=1.C[C:24]1[C:33]([NH2:34])=[C:32]2[C:27]([C:28](SC)=[N:29][CH:30]=[N:31]2)=[CH:26][CH:25]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1>CC(O)=O.O1CCOCC1>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[N:12]1[CH:11]=[N:10][C:9]2[C:13]1=[N:14][CH:15]=[N:16][C:8]=2[C:7]1[C:2]([C:30]2[N:29]=[CH:28][C:27]3[C:32](=[C:33]([NH2:34])[CH:24]=[CH:25][CH:26]=3)[N:31]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 444791786-(2-Fluoropyridin-3-YL)-9-(tetrahydro-2H-pyran-2-YL)-9H-purineHCID 596273877-Methyl-4-(methylthio)quinazolin-8-amine

生成物 1

HCID 86649314HCID 86649314、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

A 250 ml flask was charged with 6-(2-fluoropyridin-3-yl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (2.92 g, 9.74 mmol) and 7-methyl-4-(methylthio)quinazolin-8-amine (2.00 g, 9.74 mmol) along with 20 ml of dioxane. 1.0 M LiHMDS in THF (29.2 ml, 29.2 mmol) was then added dropwise at RT. The reaction was stirred for 6 hrs and then treated with 5 ml of HOAc. The volatiles were removed under vacuum. The residue was dissolved in chloroform and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel eluting with a gradient of 20 to 60% EtOAc in hexanes to give 7-methyl-4-(methylthio)-N-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylquinazolin-8-amine as a yellow solid. MS Found: (ESI pos. ion) m/z 485 (M+H+).

後処理

  1. customThe volatiles were removed under vacuum
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. custompurified by column chromatography on silica gel eluting with a gradient of 20 to 60% EtOAc in hexanes

出典と根拠

ORDレコード
ord-fccfe8f3a46145608d97893a85e11149
出典データセット
uspto-grants-2013_10
特許番号
US08557830B2

反応ノート

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