Methylamine → 1-(5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)-N-methylmethanamine

HRID 1692753Notes

Reaction equation

HRID 1692753 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[N:10]=[C:9]([CH:11]=O)[S:8][C:6]=2[N:7]=1.[CH3:19][NH2:20]>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[N:10]=[C:9]([CH2:11][NH:20][CH3:19])[S:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 576854055-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

Product 1

HCID 576854121-(5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)-N-methylmethanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Also, to a solution of 5-chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde 44 in 50 mL THF was added 20 mL of 40% methylamine in water. The reaction mixture was stirred at room temperature 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 temperature 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 of 1-(5-chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)-N-methylmethanamine 61.

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 temperature 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-82ebc97a0fa9431bbb0af8c77573a03d
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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