2,4-Bis-benzyloxy-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidine → 5-Isopropyl-6-(2,3,5-trimethyl-phenoxy)-1H-pyrimidine-2,4-dione

HRID 426260노트

반응식

HRID 426260 반응식
C([O:8][C:9]1[N:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([CH:23]([CH3:25])[CH3:24])=[C:11]([O:26][C:27]2[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[C:28]=2[CH3:35])[N:10]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[CH:23]([C:12]1[C:13](=[O:15])[NH:14][C:9](=[O:8])[NH:10][C:11]=1[O:26][C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[C:28]=1[CH3:35])([CH3:25])[CH3:24]

참가 물질

6

반응물 2

HCID 591848362,4-Bis-benzyloxy-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 591848065-Isopropyl-6-(2,3,5-trimethyl-phenoxy)-1H-pyrimidine-2,4-dione수율 59%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

2,4-Bis-benzyloxy-5-isopropyl-6-(2,3,5-trimethyl-phenoxy)-pyrimidine was dissolved in 6 mL ethyl acetate and 6 mL ethanol mixture. 10% Pd/C (52 mg) was added to the mixture. Then hydrogen balloon was applied. The reaction was stirred at room temperature for 40 minutes. The reaction crude was filtered through celite. The filtrate was concentrated down and purified (silica gel, 0-50% EtOAC/hexane) followed by reverse phase HPLC (MeCN/water) to give white solid (94 mg, 59%). LC-MS shows 289.1 (M+1). 1H NMR (300 MHz, CDCl3): δ 9.6 (br, 1H), 8.9 (br, 1H), 6.88 (s, 1H), 6.58 (s, 1H), 3.12 (m, 1H), 2.18 (s, 6H), 2.12 (s, 3H), 1.22 (d, 6H).

후처리

  1. customThe reaction crude
  2. filtrationwas filtered through celite
  3. concentrationThe filtrate was concentrated down
  4. custompurified (silica gel, 0-50% EtOAC/hexane)

출처 및 근거

ORD 기록
ord-d55aaa821c174f1888650d07e3e8dba9
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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