Sodium methanethiolate → 2-amino-6-furan-2-yl-5-methyl-3H-pyrimidin-4-one

HRID 1356012

반응식

HRID 1356012 반응식
[NH2:1][C:2]1[N:7]=[C:6]([O:8]S(C(F)(F)F)(=O)=O)[C:5]([CH3:16])=[C:4]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1.C[S-].[Na+]>COCCOC>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([CH3:16])=[C:4]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1

참가 물질

4

반응물 2

HCID 4378561Sodium methanethiolateHCID 86583753Trifluoromethanesulfonic acid 2-amino-6-furan-2-yl-5-methyl-pyrimidin-4-yl ester

생성물 1

HCID 1354024582-amino-6-furan-2-yl-5-methyl-3H-pyrimidin-4-one수율 24.5%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

A stirred solution of 250 mg (0.77 mmol) trifluoromethanesulfonic acid 2-amino-6-furan-2-yl-5-methyl-pyrimidin-4-yl ester and 217 mg (3.09 mmol) sodium methanethiolate in 10 ml dry DME under argon was heated at 80° C. for 2 hours. The reaction mixture was then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was triturated in ethyl acetate/ether and the crystals collected by filtration to afford 36 mg (24%) 2-amino-6-furan-2-yl-5-methyl-3H-pyrimidin-4-one as a yellow crystalline solid. The mother liquor was concentrated in vacuo and the residue triturated in ether/hexane and the crystals collected by filtration to afford 13 mg (8%) 4-furan-2-yl-5-methyl-6-methylsulfanyl-pyrimidin-2-ylamine as a yellow crystalline solid. EI-MS m/e (%): 221 (M+, 76), 188 ([M—SH]+, 100).

후처리

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in ethyl acetate/ether
  6. filtrationthe crystals collected by filtration

출처 및 근거

ORD 기록
ord-e9d9b60027a54757bebf87e1c52ba0ee
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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