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Morpholine → 2-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

HRID 645513
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인쇄 미리보기

반응식

HRID 645513 반응식
C([O:4][C:5]([C:7]1[C:8]([O:15][CH2:16][CH:17]2[CH2:24][CH2:23][C:20]3([CH2:22][CH2:21]3)[CH2:19][CH2:18]2)=[N:9][C:10]([C:13]#[N:14])=[N:11][CH:12]=1)=[O:6])C=C.N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]([C:10]1[N:9]=[C:8]([O:15][CH2:16][CH:17]2[CH2:24][CH2:23][C:20]3([CH2:22][CH2:21]3)[CH2:19][CH2:18]2)[C:7]([C:5]([OH:6])=[O:4])=[CH:12][N:11]=1)#[N:14]
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참가 물질

5

반응물 2

HCID 8083MorpholineHCID 687066042-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

생성물 1

HCID 687069622-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of a 2-cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester (0.096 mmol) in THF (1.0 mL) are added Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium) (0.0096 mmol) and morpholine (0.19 mmol) at room temperature. The reaction mixture is stirred at room temperature for 0.5 h and the reaction is quenched by the addition of sat. aq. NaHCO3. The mixture is extracted with ether. The aqueous layer is acidified to pH 2 with sat. aq. KHSO4. The mixture is extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude titled compound.

후처리

  1. customthe reaction is quenched by the addition of sat. aq. NaHCO3
  2. extractionThe mixture is extracted with ether
  3. extractionThe mixture is extracted with AcOEt
  4. washThe organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1360f99a564e4119b2fce54cea85024d
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07704996B2

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