p-Toluenesulfonic acid → 7-Benzyl-N-(3-(isoquinolin-3-yl)-4-methylphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

HRID 1890736Notes

Reaction equation

HRID 1890736 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](Cl)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]([C:29]2[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=2[CH3:36])[NH2:32])[N:20]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([NH:32][C:31]3[CH:33]=[CH:34][C:35]([CH3:36])=[C:29]([C:21]4[N:20]=[CH:19][C:28]5[C:23]([CH:22]=4)=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:30]=3)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 219588387-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidineHCID 583178853-(Isoquinolin-3-yl)-4-methylaniline

Product 1

HCID 583179587-Benzyl-N-(3-(isoquinolin-3-yl)-4-methylphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a reaction vessel containing 7-benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (518 mg, 2 mmol), 3-(isoquinolin-3-yl)-4-methylaniline (470 mg, 2 mmol), pTSA (144 mg, 0.6 mmol) is added isopropanol (7 ml). The vessel is purged with nitrogen, sealed. The reaction vessel is placed in a microwave reactor and irradiated for 30 minutes at 130° C. The reaction mixture is cooled to room temperature and diluted with ethyl acetate. It is washed with saturated aqueous NaHCO3, water and brine, dried over anhydrous MgSO4 and concentrated. The residue is subjected to silica gel flash chromatography (2% methanol in dichloromethane) to afford 7-Benzyl-N-(3-(isoquinolin-3-yl)-4-methylphenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine as a brown solid. LC-MS m/z: 458.2 (M+1).

Workup

  1. customThe vessel is purged with nitrogen
  2. customsealed
  3. customThe reaction vessel is placed in a microwave reactor
  4. customirradiated for 30 minutes at 130° C
  5. additiondiluted with ethyl acetate
  6. washIt is washed with saturated aqueous NaHCO3, water and brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1a14e5057a7746249edebdf8bc5c2ed3
Source dataset
uspto-grants-2013_08
Patent number
US08507491B2

Reaction notes

Loading…