Phenethylamine → 4-(N-benzylmethylamino)-2-methyl-6-oxo-7-phenyl-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidine

HRID 1728552ノート

反応式

HRID 1728552 の反応式
[NH:1]([C:8]1[C:13]([CH2:14][C:15]([O:17]C)=O)=[C:12](Cl)[N:11]=[C:10]([CH3:20])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([CH2:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([CH2:28][NH:29][C:12]1[C:13]2[CH2:14][C:15](=[O:17])[N:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:8]=2[N:9]=[C:10]([CH3:20])[N:11]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

3

反応物 2

HCID 1001PhenethylamineHCID 86747976HCID 86747976、化合物

生成物 1

HCID 190143314-(N-benzylmethylamino)-2-methyl-6-oxo-7-phenyl-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidine収率 44.6%

反応条件

温度
160 °C

実験手順

A mixture of 4-anilino-6-chloro-2-methylpyrimidine-5-acetic acid, methyl ester (5.0g, 17.2mM) and benzylmethylamine (2.22ml, 17.2mM) was heated at 160° C. for 3.5 hours. The mixture was cooled and then partitioned between methylene chloride (50ml) and 2M hydrochloric acid (50ml). The organic layer was separated, washed with a solution of sodium hydroxide (2M, 50ml), water, dried and the solvent evaporated. The residue was purified by flash column chromatography on silica (Merck 9385), eluting with ethyl acetate/hexane (20:80, v/v) to give 4-(N-benzylmethylamino)-2-methyl-6-oxo-7-phenyl-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidine (2.64g, 44.6%) m.p. 81°-84° C.; microanalysis, found; C, 73.0; H, 6.0; N, 16.3%; C21H20H40 requires C, 73.3; H, 5.8; N, 16.3%; NMR: DMSOd6 : 2.3(3H, s, pyrimidine-CH3), 3.2(3H,s,N-CH3), 3.95(2H,s,COCH2), 4.85(2H,s,N-CH2), 7.2-7.55(10H, complex, aromatic).

後処理

  1. temperatureThe mixture was cooled
  2. custompartitioned between methylene chloride (50ml) and 2M hydrochloric acid (50ml)
  3. customThe organic layer was separated
  4. washwashed with a solution of sodium hydroxide (2M, 50ml), water
  5. customdried
  6. customthe solvent evaporated
  7. customThe residue was purified by flash column chromatography on silica (Merck 9385)
  8. washeluting with ethyl acetate/hexane (20:80

出典と根拠

ORDレコード
ord-914c25346ab64951a8a16fc36e8d38ab
出典データセット
uspto-grants-1994_07
特許番号
US05328910

反応ノート

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