Triphenylphosphine → 5-bromo-1-[2, 6-difluorobenzyl]-3-{3-acetoxy-2(R)-phenylpropyl}-6-methylpyrimidine-2,4(1H,3H)-dione

HRID 1766047노트

반응식

HRID 1766047 반응식
O[CH2:2][C@@H:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][O:5][C:6](=[O:8])[CH3:7].[Br:15][C:16]1[C:17](=[O:33])[NH:18][C:19](=[O:32])[N:20]([CH2:23][C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=2[F:31])[C:21]=1[CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C1COCC1>[Br:15][C:16]1[C:17](=[O:33])[N:18]([CH2:2][C@@H:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][O:5][C:6](=[O:8])[CH3:7])[C:19](=[O:32])[N:20]([CH2:23][C:24]2[C:25]([F:31])=[CH:26][CH:27]=[CH:28][C:29]=2[F:30])[C:21]=1[CH3:22]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 10997888acetic acid 3-hydroxy-2-(R)-phenyl-propyl esterHCID 120945185-Bromo-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione

생성물 1

HCID 210183995-bromo-1-[2, 6-difluorobenzyl]-3-{3-acetoxy-2(R)-phenylpropyl}-6-methylpyrimidine-2,4(1H,3H)-dione수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of acetic acid 3-hydroxy-2-(R)-phenyl-propyl ester (1.87 g, 9.64 mmol) in THF (50 mL) was treated with 5-bromo-1-(2,6-difluorobenzyl)-6-methyluracil 4d.1 (3.19 g, 9.64 mmol) and triphenylphosphine (3.16 g, 12.1 mmol) at ambient temperature, then di-tert-butylazodicarboxylate (2.77 g, 12.1 mmol) was introduced. The reaction mixture was stirred at ambient temperature for 16 h and volatiles were evaporated. The residue was partitioned between saturated NaHCO3/H2O and EtOAc. The organic layer was dried (sodium sulfate), evaporated, purified by flash chromatography (silica, 33% EtOAc/hexanes) to give compound 8a (4.54 g, 93%). MS (CI) m/z 508.1 and 509.0 (MH+).

후처리

  1. customvolatiles were evaporated
  2. customThe residue was partitioned between saturated NaHCO3/H2O and EtOAc
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customevaporated
  5. custompurified by flash chromatography (silica, 33% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-678d2612165144ad924e4d6b15e2e687
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07229995B2

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