Methyl iodide → 4-Methylthiopyrido[4,3-d]pyrimidine

HRID 50776Notes

Reaction equation

HRID 50776 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][N:9]=[CH:10][C:5]=2[C:4](=[S:11])[NH:3][CH:2]=1.[CH2:12](N(CC)CC)C.IC>CS(C)=O>[CH3:12][S:11][C:4]1[C:5]2[CH:10]=[N:9][CH:8]=[CH:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 178527905HCID 178527905, compound

Product 1

HCID 106548874-Methylthiopyrido[4,3-d]pyrimidineYield 156.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3H-pyrido[4,3-d]pyrimidin-4-thione (676 mg, 4.14 mmol), triethylamine (1.4 mL, 10.31 mmol), DMSO (4 mL), and iodomethane (0.48 mL, 7.72 mmol) is stirred for 12 h under N2 at 25° C. The mixture is poured onto water and extracted with EtOAc. The organic extracts are dried (MgSO4), and the solvent is removed under reduced pressure to yield 4-methylthiopyrido[4,3-d]pyrimidine (1.15 g, quant.) as a brown solid. 1H NMR (DMSO) δ 9.52 (1H, s), 9.16 (1H, s), 8.95 (1H, d, J=6 Hz), 7.86 (1H, d, J=8 Hz), 2.75 (1H, s).

Workup

  1. additionThe mixture is poured onto water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts are dried (MgSO4)
  4. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-c94097e994344d5299ddc8bff6bdfbf6
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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