m-Chloroperbenzoic acid → 4'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidine

HRID 2359733노트

반응식

HRID 2359733 반응식
[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)=[CH:9][N:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>C(Cl)Cl>[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17]([CH3:18])=[O:27])[N:12]=3)=[CH:9][N:8]=[CH:7][N:6]=2)[CH2:2][CH2:3]1

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 679837614'-(Cyclopropylmethyl)-2-(methylsulfanyl)-4,5'-bipyrimidine

생성물 1

HCID 679831774'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4′-(cyclopropylmethyl)-2-(methylsulfanyl)-4,5′-bipyrimidine (4a) (62.5 mg, 0.242 mmol) in DCM (968 μl), mCPBA (65.1 mg, 0.290 mmol) was added and the reaction mixture was stirred at rt for 1 hour. The crude reaction mixture was partitioned between saturated sodium bicarbonate solution and DCM. The aqueous layer was separated and back-extracted twice with DCM. The combined organic extracts were washed with brine, dried over sodium sulfate, then concentrated in vacuo. The crude product was carried on to the next step without further purification. MS (ES+): m/z=275.2 (100) [MH+]. HPLC: tR=0.72 minute over 3 minutes. Purity: 100% [HPLC (LC/MS) at 220 nm].

후처리

  1. customThe crude reaction mixture
  2. customwas partitioned between saturated sodium bicarbonate solution and DCM
  3. customThe aqueous layer was separated
  4. extractionback-extracted twice with DCM
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was carried on to the next step without further purification
  9. waitHPLC: tR=0.72 minute over 3 minutes

출처 및 근거

ORD 기록
ord-1ceb9c9877844a778ec3275af32cf489
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685993B2

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