Tetrahydrofuran → HCID 86649314, 화합물

HRID 1042294노트

반응식

HRID 1042294 반응식
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

참가 물질

7

반응물 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

생성물 1

HCID 86649314HCID 86649314, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 312751,4-Dioxane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-fccfe8f3a46145608d97893a85e11149
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557830B2

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