Methylamine → N-[4-(methylthio)thieno[2,3-d]pyrimidin-6-ylmethylidene]methanamine

HRID 1453672Notes

Reaction equation

HRID 1453672 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[CH:11]=[C:10]([CH:12]=O)[S:9][C:5]=2[N:6]=[CH:7][N:8]=1.[CH3:14][NH2:15].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH3:1][S:2][C:3]1[C:4]2[CH:11]=[C:10]([CH:12]=[N:15][CH3:14])[S:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 179658594-(Methylthio)thieno[2,3-d]pyrimidine-6-carbaldehyde

Product 1

HCID 69059019N-[4-(methylthio)thieno[2,3-d]pyrimidin-6-ylmethylidene]methanamineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(Methylthio)thieno[2,3-d]pyrimidine-6-carbaldehyde (13 g), methylamine (33% in EtOH, 20.6 mL) and anhydrous MgSO4 (20 g) was stirred in DCM (465 ml) for 2 days at ambient temperature under an inert atmosphere. The reaction mixture was filtered then concentrated in vacuo to afford the title compound as a brown solid (13.8 g, 100%);

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-ad9a625df2254fcf978fa0bdf9035fe2
Source dataset
uspto-grants-2009_01
Patent number
US07476677B2

Reaction notes

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