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

HRID 1356012

反応式

HRID 1356012 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e9d9b60027a54757bebf87e1c52ba0ee
出典データセット
uspto-grants-2003_07
特許番号
US06586441B2

関連ノート

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