Hydrochloric Acid → 3-Methylthio-8-oxo-6-(2-methoxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine

HRID 728029ノート

反応式

HRID 728029 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH2:7])=[NH:6].Cl.[CH3:13][S:14][C:15]1[N:16]=[N:17][C:18]([C:22](OCC)=[O:23])=[C:19](Cl)[N:20]=1.C(N(CC)CC)C>C(#N)C>[CH3:13][S:14][C:15]1[N:16]=[N:17][C:18]2[C:22](=[O:23])[NH:7][C:5]([C:4]3[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=3[O:2][CH3:1])=[N:6][C:19]=2[N:20]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 43218342-Methoxy-benzamidineHCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-Carboxylate

生成物 1

HCID 1356707853-Methylthio-8-oxo-6-(2-methoxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
0 °C

実験手順

A cooled (0° C.) solution of 2-methoxybenzamidine (from 1.97 g of the hydrochloride) in acetonitrile (17 ml) was added to a cooled solution of 3-methylthio-5-chloro-6-carboethoxy-1,2,4-triazine (prepared from 3-methylthio-5-oxo-6-carboethoxy-4,5-dihydro-1,2,4-triazine, 1.08 g, and thionyl chloride, 20 ml) in acetonitrile (17 ml). Triethylamine (0.51 g) was added and the reaction mixture was stirred with cooling (0° C.) for one hour and then at ambient temperature for 17 hours to afford a yellow solid which was washed with acetonitrile and ether to afford the crude title compound (1.39 g). A sample (0.35 g) of this was washed twice with boiling methanol to afford the title compound, 0.25 g, m.p. 267.5°-268.5° C. The remaining material (1.04 g) was similarly treated with boiling methanol to afford the title compound, 0.91 g, m.p. 266°-268° C.

後処理

  1. customat ambient temperature for 17 hours to afford a yellow solid which
  2. washwas washed with acetonitrile and ether
  3. customto afford the crude title compound (1.39 g)
  4. washA sample (0.35 g) of this was washed twice with boiling methanol

出典と根拠

ORDレコード
ord-3c00af590a2c403dbbd1649498e33327
出典データセット
uspto-grants-1991_09
特許番号
US05047404

反応ノート

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