Methylamine → HCID 59592917, compound

HRID 881220Notes

Reaction equation

HRID 881220 reaction equation
[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[CH:10]=[C:9]([CH:11]=O)[S:8][C:6]=2[N:7]=1.[CH3:19][NH2:20]>C1(C)C=CC=CC=1.C1COCC1.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[CH:10]=[C:9]([CH2:11][NH:20][CH3:19])[S:8][C:6]=2[N:7]=1

Participants

6

Reactant 2

HCID 6329MethylamineHCID 568338442-Chloro-4-morpholinothieno[2,3-d]pyrimidine-6-carbaldehyde

Product 1

HCID 59592917HCID 59592917, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-chloro-4-morpholinothieno[2,3-d]pyrimidine-6-carbaldehyde (2.0 g) in 50 mL toluene and 50 mL THF was added 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 MeOH 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 (2-chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)-N-methylmethanamine (53% yield). MS (Q1) 300 (M+).

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in 50 mL MeOH
  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)

Sources & evidence

ORD record
ord-9daba9c1027c41d5a43c6d2cf0549a01
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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