Dichloromethane → N-(2-chloropyridin-4-yl)-4-(2-{[1-(methoxymethyl)propyl]amino}pyridin-4-yl)pyrimidin-2-amine

HRID 2389561Notes

Reaction equation

HRID 2389561 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:22][O:23][CH2:24][CH:25]([NH2:28])[CH2:26][CH3:27].ClCCl>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:28][CH:25]([CH2:24][O:23][CH3:22])[CH2:26][CH3:27])[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 938372-Butanamine, 1-methoxy-HCID 86644113N,4-bis(2-chloropyridin-4-yl)pyrimidin-2-amine

Product 1

HCID 25102830N-(2-chloropyridin-4-yl)-4-(2-{[1-(methoxymethyl)propyl]amino}pyridin-4-yl)pyrimidin-2-amineYield 199%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

300 mg of N,4-bis(2-chloropyridin-4-yl)pyrimidin-2-amine (0.94 mmol), 486 mg of 1-methoxybutan-2-amine (4.71 mmol), were heated at 240° C. for 90 minutes under micro-waves irradiation in 0.6 ml of 1-Methyl-2-pyrrolidinone. After cooling, the reaction mixture was poured into 10 ml of dichloromethane, washed twice with 5 ml of water. After drying over magnesium sulfate, filtration and concentration in vacuo, the crude product was chromatographed on silica (ethyl acetate/heptane) to yield 0.72 g of N-(2-chloropyridin-4-yl)-4-(2-{[1-(methoxymethyl)propyl]amino}pyridin-4-yl)pyrimidin-2-amine (yield=19%).

Workup

  1. temperatureAfter cooling
  2. washwashed twice with 5 ml of water
  3. dry with materialAfter drying over magnesium sulfate, filtration and concentration in vacuo
  4. customthe crude product was chromatographed on silica (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-332f28e7071e4e07bd216dbecab15ba0
Source dataset
uspto-grants-2012_09
Patent number
US08273759B2

Reaction notes

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