N,N'-Dimethylethylenediamine → 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-1-(4-tert-butylphenyl)-4-methylpyridin-2(1H)-one

HRID 632834

反応式

HRID 632834 の反応式
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]3[C:13](=[O:19])[NH:14][CH:15]=[CH:16][C:17]=3[CH3:18])[CH2:9][CH2:8][C:6]=2[N:7]=1.[C:20]([C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21].CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN1C(=O)CCC1.[Cu]I>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]3[C:13](=[O:19])[N:14]([C:27]4[CH:28]=[CH:29][C:24]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:25][CH:26]=4)[CH:15]=[CH:16][C:17]=3[CH3:18])[CH2:9][CH2:8][C:6]=2[N:7]=1

参加物

7

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 1420291-tert-Butyl-4-iodobenzeneHCID 1212495913-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpyridin-2(1H)-one

生成物 1

HCID 1212495483-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-1-(4-tert-butylphenyl)-4-methylpyridin-2(1H)-one収率 57%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
70 °C

実験手順

A mixture of 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpyridin-2(1H)-one, 1-tert-butyl-4-iodobenzene (0.071 mL, 0.40 mmol), N,N′-dimethylethylenediamine (0.022 mL, 0.20 mmol), potassium phosphate tribasic (170 mg, 0.80 mmol), copper (I) iodide (15 mg, 0.080 mmol) in 1.0 mL NMP was heated at 70° C. for 17 hours. The reaction mixture was partitioned between EtOAc and aqueous NaHCO3 solution, the EtOAc layer washed with H2O, brine, dried with anhydrous Na2SO4 and rotary evaporated. The resulting oil was chromatographed eluting with CHCl3, then CHCl3/EtOAc (1:1), and then gradient 3% to 6% MeOH in CHCl3/EtOAc (1:1). The solid obtained was then precipitated from an EtOAc/hexane mixture to give a pale yellow solid (44 mg, 57%). 1H NMR (DMSO) δ: 7.94 (s, 1H), 7.48-7.53 (m, 2H), 7.43 (d, J=6.7 Hz, 1H), 7.27-7.33 (m, 2H), 6.30 (s, 2H), 6.19 (d, J=7.0 Hz, 1H), 3.98 (br. s, 2H), 3.31 (br. s, 2H), 2.68 (t, J=5.3 Hz, 2H), 2.19 (s, 3H), 1.32 (s, 9H)

後処理

  1. customThe reaction mixture was partitioned between EtOAc and aqueous NaHCO3 solution
  2. washthe EtOAc layer washed with H2O, brine
  3. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  4. customThe resulting oil was chromatographed
  5. washeluting with CHCl3
  6. customThe solid obtained
  7. customwas then precipitated from an EtOAc/hexane mixture

出典と根拠

ORDレコード
ord-5a1fc918034c4ffa837926e5e558df51
出典データセット
uspto-grants-2016_04
特許番号
US09321766B1

関連ノート

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