4-Methylphenyl isocyanate → 4-(5-Amino-2-(pyridin-3-yl)thiazolo[5,4-d]pyrimidin-7-yl)-N-(p-tolyl)piperazine-1-carboxamide

HRID 718270Notes

Reaction equation

HRID 718270 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[S:8][C:6]=2[N:7]=1.[C:23]1([CH3:32])[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1>O1CCOCC1>[NH2:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:18][CH2:19][N:20]([C:30]([NH:29][C:26]3[CH:27]=[CH:28][C:23]([CH3:32])=[CH:24][CH:25]=3)=[O:31])[CH2:21][CH2:22]2)[C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[S:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 509420567-(Piperazin-1-yl)-2-(pyridin-3-yl)thiazolo[5,4-d]pyrimidin-5-amine

Product 1

HCID 469163824-(5-Amino-2-(pyridin-3-yl)thiazolo[5,4-d]pyrimidin-7-yl)-N-(p-tolyl)piperazine-1-carboxamideYield 79.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 5-amino-7-(piperazin-1-yl)-2-(pyridine-3-yl)thiazolo[5,4-d]pyrimidine (150 mg, 0.48 mmol) in dioxane (10 ml) was added 4-tolyl isocyanate (63 μl, 0.5 mmol). The resulting reaction mixture was stirred at room temperature for 30 minutes. The solvents were evaporated in vacuo and the residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1/25), yielding the pure title compound as a yellowish solid (170 mg, 79%).

Workup

  1. customThe resulting reaction mixture
  2. customThe solvents were evaporated in vacuo
  3. customthe residue was purified by flash chromatography on silica
  4. additiona mixture of methanol and dichloromethane (in a ratio of 1/25),

Sources & evidence

ORD record
ord-9e1be929a6454bfea2259600a36d84a2
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

Loading…