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

HRID 41892

반응식

HRID 41892 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-fdcd8acac1394311b9988989ddd68e8f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536161B2

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