m-Chloroperbenzoic acid → 4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine 1-oxide

HRID 532750노트

반응식

HRID 532750 반응식
[Cl:1][C:2]1[C:3]2[CH2:10][CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.C1C=C(Cl)C=C(C(OO)=[O:19])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N+:5]([O-:19])=[C:4]2[CH2:8][CH2:9][CH2:10][C:3]=12

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 133124494-chloro-5H,6H,7H-cyclopenta[d]pyrimidine

생성물 1

HCID 142310914-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine 1-oxide수율 47%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

To a solution of 4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine (5.69 g, 36.8 mmol) in chloroform (200 mL) was added MCPBA (19 g, 84.8 mmol) in chloroform (50 mL) dropwise. The mixture was stirred at room temperature for 16 hour. After cooling with ice-water, the mixture was quenched with Na2S2O3 (27.5 g) in water (110 mL) dropwise and followed by Na2CO3 (14 g) in water (52 mL) dropwise. The organic phase was separated and the aqueous phase was extracted with chloroform (3×200 mL). The organic phase was dried and concentrated at low temperature (<25° C.). The residue was subject to chromatography on silica gel, eluting by ethyl acetate to afford 4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine 1-oxide (2.93 g, 47%). MS (APCI+) [M+H] +171.

후처리

  1. customthe mixture was quenched with Na2S2O3 (27.5 g) in water (110 mL) dropwise
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with chloroform (3×200 mL)
  4. customThe organic phase was dried
  5. concentrationconcentrated at low temperature (<25° C.)
  6. washeluting by ethyl acetate

출처 및 근거

ORD 기록
ord-97ce143727fe419da1e8bfdf6a7fdc10
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853199B2

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