Water → HCID 59514499, compound

HRID 2422155Notes

Reaction equation

HRID 2422155 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([N:13]([CH3:15])[CH3:14])[N:5]=[C:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)=[O:25])=[CH:19][CH:18]=2)[N:3]=1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.O>CN1C(=O)N(C)CCC1>[CH3:14][N:13]([CH3:15])[C:6]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:2]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[N:3]=[C:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)=[O:25])=[CH:19][CH:18]=2)[N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 59514494HCID 59514494, compound

Product 1

HCID 59514499HCID 59514499, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
150 °C

Procedure

A mixture of methyl {4-chloro-6-(dimethylamino)-2-[4-(2-naphthoylamino)benzyl]pyrimidin-5-yl}acetate (0.094 g, 0.19 mmol) and morpholine (0.048 mL, 0.55 mmol) in DMPU (2 mL) was heated at 150° C. in a sealed tube for 15 hours. After cooling to room temperature, the reaction mixture was poured into water and extracted with EtOAc. The combined organic extracts was washed sequentially with 1N HCl, saturated NaHCO3, and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product thus obtained was chromatographed over silica gel eluting with 5% EtOAc in CH2Cl2 to give methyl {4-(dimethylamino)-6-morpholin-4-yl-2-[4-(2-naphthoylamino)benzyl]pyrimidin-5-yl}acetate (0.096 g, 95% yield) as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts was washed sequentially with 1N HCl, saturated NaHCO3, and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product thus obtained
  8. customwas chromatographed over silica gel eluting with 5% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-619bf50f52294364867a0146e0883b2d
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

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