Trimethylamine → 4-(Dimethylamino)butyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate

HRID 445057ノート

反応式

HRID 445057 の反応式
Cl.[NH2:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][CH:12]=2)=[C:5]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:4]=1.CS(O)(=O)=O.S(Cl)(Cl)=O.[CH3:36][N:37]([CH3:43])[CH2:38][CH2:39][CH2:40][CH2:41]O.CN(C)C>C(#N)C.C(OCC)(=O)C>[NH2:2][C:3]1[N:8]=[C:7]([CH3:9])[C:6]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][C:18]([O:20][CH2:41][CH2:40][CH2:39][CH2:38][N:37]([CH3:43])[CH3:36])=[O:19])=[CH:15][CH:16]=2)=[C:5]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:4]=1

参加物

8

反応物 5

HCID 1146TrimethylamineHCID 6395Methanesulfonic AcidHCID 24386Thionyl ChlorideHCID 833504-(Dimethylamino)butan-1-olHCID 684321402-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetic acid hydrochloride

生成物 1

HCID 497799954-(Dimethylamino)butyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

The solution of the product from step (vi) (2.00 g, 5.28 mmol) and methanesulfonic acid (1.52 g, 15.8 mmol) in acetonitrile (16.0 g) was cooled to 20° C. and thionyl chloride (0.94 g, 7.92 mmol) was slowly added to the solution. After the mixture was stirred at 20° C. for 30 minutes, 4-dimethylamino-1-butanol (1.11 g, 9.50 mmol) was slowly added to the mixture. The mixture was heated to 40° C. and stirred at the temperature for 5 hours. After the reaction mixture was cooled to 20° C., ethyl acetate (18.0 g) and 25% aq. trimethylamine (18.0 g) was slowly added to the mixture. The organic layer was separated and washed respectively with 5% aq. NH4Cl (20.0 g), 1% aq. NaCl (20.0 g) and water (20.0 g). The solution of the subtitle compound was used in the next step without concentration.

後処理

  1. temperatureThe mixture was heated to 40° C.
  2. stirringstirred at the temperature for 5 hours
  3. temperatureAfter the reaction mixture was cooled to 20° C.
  4. customThe organic layer was separated
  5. washwashed respectively with 5% aq. NH4Cl (20.0 g), 1% aq. NaCl (20.0 g) and water (20.0 g)
  6. concentrationThe solution of the subtitle compound was used in the next step without concentration

出典と根拠

ORDレコード
ord-5b88fec0d4e94b69bf685873026f6af2
出典データセット
uspto-grants-2013_07
特許番号
US08476288B2

反応ノート

読み込み中…