1,4-Diazabicyclo(2.2.2)octane--trimethylalumane (1/2) → 2-N-Methyl-2-N-phenyl-6-(5-{5H,6H,7H-pyrrolo[3,4-d]pyrimidin-6-yl}-1,2,4-oxadiazol-3-yl)-1,3,5-triazine-2,4-diamine

HRID 341440

반응식

HRID 341440 반응식
Cl.[N:2]1[C:7]2[CH2:8][NH:9][CH2:10][C:6]=2[CH:5]=[N:4][CH:3]=1.C[Al](C)C.C[Al](C)C.C1N2CCN(CC2)C1.[CH3:27][N:28]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:29]1[N:34]=[C:33]([NH2:35])[N:32]=[C:31]([C:36]2[N:40]=[C:39](C(Cl)(Cl)Cl)[O:38][N:37]=2)[N:30]=1>C1COCC1>[CH3:27][N:28]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:29]1[N:34]=[C:33]([NH2:35])[N:32]=[C:31]([C:36]2[N:40]=[C:39]([N:9]3[CH2:10][C:6]4[CH:5]=[N:4][CH:3]=[N:2][C:7]=4[CH2:8]3)[O:38][N:37]=2)[N:30]=1

참가 물질

5

반응물 3

HCID 166883661,4-Diazabicyclo(2.2.2)octane--trimethylalumane (1/2)HCID 547588476,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine hydrochlorideHCID 66802564N-methyl-N-phenyl-6-(5-trichloromethyl-[1,2,4]oxadiazol-3-yl)-[1,3,5]triazine-2,4-diamine2회

생성물 1

HCID 569419812-N-Methyl-2-N-phenyl-6-(5-{5H,6H,7H-pyrrolo[3,4-d]pyrimidin-6-yl}-1,2,4-oxadiazol-3-yl)-1,3,5-triazine-2,4-diamine수율 8.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine hydrochloride salt (38 mg, 0.231 mmol) in anhydrous THF (3 mL) was added DABAL-Me3 (bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]-octane) (57 mg, 0.231 mmol) at room temperature. The solution was heated under nitrogen at 40 C for 3 h and N-methyl-N-phenyl-6-(5-trichloromethyl-[1,2,4]oxadiazol-3-yl)-[1,3,5]triazine-2,4-diamine (Intermediate 60, 60 mg, 0.155 mmol) was added. The resulting reaction mixture was heated at 80 C for 5 h and then quenched with water (2 mL) drop-wise. The solution was extracted into EtOAc (3×25 mL) and the combined organics washed with a 1M aq. solution of HCl (20 mL), brine (20 mL), dried over magnesium sulfate, evaporated to dryness and purified by preparative HPLC-MS (Method B) to afford the title compound as a white solid (5 mg, 8%).

후처리

  1. temperatureThe solution was heated under nitrogen at 40 C for 3 h
  2. customThe resulting reaction mixture
  3. temperaturewas heated at 80 C for 5 h
  4. customquenched with water (2 mL) drop-wise
  5. extractionThe solution was extracted into EtOAc (3×25 mL)
  6. washthe combined organics washed with a 1M aq. solution of HCl (20 mL), brine (20 mL)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness
  9. custompurified by preparative HPLC-MS (Method B)

출처 및 근거

ORD 기록
ord-a8746bf53f9b45dbaec911bf523476bf
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895733B2

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