Methylamine → 1-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine

HRID 41892

反応式

HRID 41892 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.C1COCC1.[CH3:24][NH2:25]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][NH:25][CH3:24])=[CH:8][C:6]=2[N:7]=1

参加物

6

反応物 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

生成物 1

HCID 595929371-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)-N-methylmethanamine収率 53%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

2-Chloro-4-morpholinothieno[3,2-c]pyrimidine-6-carbaldehyde 10 (2.0 g) was dissolved in 50 mL toluene and 50 mL THF followed by the addition of 20 mL of 40% methylamine in H2O. The reaction mixture was stirred at room temp under N2 for 24 hours. The solvents were removed in vacuo and the residue was dissolved in 50 mL methanol and 50 mL THF and the NaBH4 added portion-wise. This reaction mixture was stirred at room temp under N2 for 24 hours and complete reaction was confirmed by LCMS. The solvents were removed in vacuo and the crude product purified by flash chromatography (EtOAc/EtOH) to give 1.12 g 35 (53% yield). MS (Q1) 300 (M+).

後処理

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in 50 mL methanol
  3. stirringThis reaction mixture was stirred at room temp under N2 for 24 hours
  4. customcomplete reaction
  5. customThe solvents were removed in vacuo
  6. customthe crude product purified by flash chromatography (EtOAc/EtOH)

出典と根拠

ORDレコード
ord-fdcd8acac1394311b9988989ddd68e8f
出典データセット
uspto-grants-2013_09
特許番号
US08536161B2

関連ノート

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