Ammonium Chloride → 6-(4-Aminophenylmethyl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1251603ノート

反応式

HRID 1251603 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[S:26][C:14]3[N:15]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:16](=[O:21])[N:17]([CH3:20])[C:18](=[O:19])[C:13]=3[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[S:26][C:14]3[N:15]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:16](=[O:21])[N:17]([CH3:20])[C:18](=[O:19])[C:13]=3[CH:12]=2)=[CH:6][CH:5]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 222580026-(4-nitrophenylmethyl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidin-2,4(1H, 3H)-dione

生成物 1

HCID 222580286-(4-Aminophenylmethyl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione収率 7.9%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

To a solution of 6-(4-nitrophenylmethyl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidin-2,4(1H, 3H)-dione (275 mg) in ethanol (15 ml) and water (1 ml) was added iron powder (82 mg) and ammonium chloride (78 mg). The mixture was heated at 90° C. for 6 h. and then allowed to cool to room temperature. The reaction was filtered and then evaporated before being partitioned between ethyl acetate and water. The organic layer was collected, dried over magnesium sulfate, and then evaporated. The resultant oil was purified by normal phase HPLC (isohexane:ethyl acetate 80-0:20-100) to give the title compound (20 mg).

後処理

  1. temperatureto cool to room temperature
  2. filtrationThe reaction was filtered
  3. customevaporated
  4. custombefore being partitioned between ethyl acetate and water
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe resultant oil was purified by normal phase HPLC (isohexane:ethyl acetate 80-0:20-100)

出典と根拠

ORDレコード
ord-52a4f3836d0043e2892a100c5bd0dffe
出典データセット
uspto-grants-2002_01
特許番号
US06342502B1

反応ノート

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