Methyl iodide → 7-Amino-4-methylthiopyrido[4,3-d]pyrimidine

HRID 1386152Notes

Reaction equation

HRID 1386152 reaction equation
[CH3:1]CN(CC)CC.[NH2:8][C:9]1[N:18]=[CH:17][C:16]2[C:15](=[S:19])[NH:14][CH:13]=[N:12][C:11]=2[CH:10]=1.CI>CS(C)=O>[NH2:8][C:9]1[N:18]=[CH:17][C:16]2[C:15]([S:19][CH3:1])=[N:14][CH:13]=[N:12][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 178507216HCID 178507216, compound

Product 1

HCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidineYield 68.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

NEt3 (6 mL, 43 mmol) is added to a solution of 7-amino-4-thiono-3H-pyrido[4,3-d]pyrimidine (0.77 g, 4.3 mmol) in DMSO (7 mL) stirred under N2 at 250C. After the two phases have been stirred for 20 min, MeI (0.26 mL, 4.2 mmol) is added. After 2 h, the reaction mixture is poured onto stirring ice-water. Solid forms instantly. After further cooling at 0° C., the solid is collected by suction filtration and dried in a vacuum oven to give 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (0.564 g, 68%). 1H NMR (DMSO) δ 8.98 (1H, s), 8.71 (1H, s), 6.94 (2H, brs), 6.49 (1H, s) 2.63 (3H, s)

Workup

  1. waitAfter 2 h
  2. additionthe reaction mixture is poured
  3. filtrationthe solid is collected by suction filtration
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-54265f70a7604630bd4363f0095a8374
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

Loading…