tert-Butyl 4-oxopiperidine-1-carboxylate → Tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)piperidine-1-carboxylate

HRID 1043609노트

반응식

HRID 1043609 반응식
[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[N:11]=[C:10]([CH2:12]P(=O)(OC)OC)[CH:9]=[CH:8][C:6]=2[N:7]=1.C([N-]C(C)C)(C)C.[Li+].[C:33]([N:40]1[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]1)([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[C:5]2[N:11]=[C:10]([CH:12]=[C:43]3[CH2:44][CH2:45][N:40]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:41][CH2:42]3)[CH:9]=[CH:8][C:6]=2[N:7]=1

참가 물질

5

반응물 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 58405032Dimethyl (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylphosphonate

생성물 1

HCID 58405028Tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of dimethyl (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylphosphonate from Example 117 (0.71 g) in anhydrous THF (15 mL) at 0° C. was added 2.0 M of lithium diisopropylamide in THF (1.4 eq). The resulting solution was allowed to warm to RT (room temperature) before adding a solution of 1-boc-4-piperidone (1.4 eq) in anhydrous THF (3 mL). The reaction mixture was stirred at room temperature for 1 h, then partitioned between brine and DCM. The organic layer was isolated, dried (MgSO4), concentrated and recrystallized from methanol. The light yellow solid was filtered and collected to give 0.72 g of tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylene)piperidine-1-carboxylate as a light yellow solid.

후처리

  1. custompartitioned between brine and DCM
  2. customThe organic layer was isolated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customrecrystallized from methanol
  6. filtrationThe light yellow solid was filtered
  7. customcollected

출처 및 근거

ORD 기록
ord-0daea6c0f6074b12a87bbcd4c4503514
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563540B2

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