Triphenylphosphine → Methyl 3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzoate

HRID 330798노트

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HRID 330798 반응식
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:37]1([CH2:43][CH2:44]O)[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N:37]1([CH2:43][CH2:44][O:1][C:2]2[CH:7]=[N:6][C:5]([C:8]3[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=3)[C:11]([O:13][CH3:14])=[O:12])=[N:4][CH:3]=2)[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59438048Methyl 3-(5-hydroxypyrimidin-2-yl)benzoate

생성물 1

HCID 58496335Methyl 3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution, kept under nitrogen, of 10.1 g (44 mmol) of methyl 3-(5-hydroxypyrimidin-2-yl)benzoate, 17.3 g (66 mmol) of triphenylphosphine and 5.9 ml (48.4 mmol) of 2-morpholin-4-ylethanol in 100 ml of THF is cooled in an ice bath, and 12.95 ml (66 mmol) of diisopropyl azodicarboxylate are slowly added dropwise with stirring. After stirring at room temperature for 2 hours, the reaction mixture is evaporated in vacuo. The residue is taken up in 100 ml of dichloromethane and 100 ml of water. The organic phase is dried over sodium sulfate and evaporated. The residue is recrystallised from isopropanol: methyl 3-[5-(2-morpholin-4-ylethoxy)pyrimidin-2-yl]benzoate as beige crystals; m.p. 89-91°; ESI 344 (M+H); HPLC: 2.06 min (method A).

후처리

  1. temperatureis cooled in an ice bath
  2. stirringAfter stirring at room temperature for 2 hours
  3. customthe reaction mixture is evaporated in vacuo
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is recrystallised from isopropanol
  7. custom2.06 min (method A)

출처 및 근거

ORD 기록
ord-2531ced09c7a48d68c3f865d1b3e3d1c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877751B2

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