(2,3-Dihydrobenzofuran-2-yl)methanamine → (6-Chloro-2-methoxy-pyrimidin-4-yl)-(2,3-dihydro-benzofuran-2-ylmethyl)-amine

HRID 216253Notes

Reaction equation

HRID 216253 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][CH:12]1[CH2:20][NH2:21].C([O-])(O)=O.[Na+]>CCO.O>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH3:10])[N:3]=[C:2]([NH:21][CH2:20][CH:12]2[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:11]2)[CH:7]=1

Participants

6

Reactant 3

HCID 29905(2,3-Dihydrobenzofuran-2-yl)methanamineHCID 516892Sodium BicarbonateHCID 120521604,6-Dichloro-2-methoxypyrimidine

Product 1

HCID 86615711(6-Chloro-2-methoxy-pyrimidin-4-yl)-(2,3-dihydro-benzofuran-2-ylmethyl)-amineYield 74.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4,6-dichloro-2-methoxy-pyrimidine (0.41 g, 2.3 mmol), C-(2,3-dihydro-benzofuran-2-yl)-methylamine (0.52 g, 3.47 mmol), and NaHCO3 (0.97 g, 12 mmol) in EtOH (7 mL) is heated to reflux for 3 h. The mixture is diluted with water (8 mL), filtered, washed (water). The solid is dissolved in EtOAc, dried (MgSO4), filtered, and concentrated in vacuo to afford (6-chloro-2-methoxy-pyrimidin-4-yl)-(2,3-dihydro-benzofuran-2-ylmethyl)-amine (0.5 g) as a solid. LCMS: RT=2.59 minutes; MS: 292 (M+H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 3 h
  3. filtrationfiltered
  4. washwashed (water)
  5. dissolutionThe solid is dissolved in EtOAc
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f637824f985437ca2038a7215147eab
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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