(3,4-dihydro-1H-isochromen-1-ylmethyl)amine → (6-Chloro-2-methoxy-pyrimidin-4-yl)-isochroman-1-ylmethyl-amine

HRID 216255Notes

Reaction equation

HRID 216255 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[CH:11]1([CH2:21][NH2:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][O:12]1.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:22][CH2:21][CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][O:12]2)[CH:7]=1

Participants

6

Reactant 3

HCID 209070(3,4-dihydro-1H-isochromen-1-ylmethyl)amineHCID 516892Sodium BicarbonateHCID 120521604,6-Dichloro-2-methoxypyrimidine

Product 1

HCID 86615712(6-Chloro-2-methoxy-pyrimidin-4-yl)-isochroman-1-ylmethyl-amineYield 109.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4,6-dichloro-2-methoxy-pyrimidine (0.45 g, 2.5 mmol), C-isochroman-1-yl-methylamine (0.53 g, 3.2 mmol), and NaHCO3 (0.63 g, 7.5 mmol) in EtOH (5 mL) is heated to reflux for 4 h. The mixture is diluted with water, concentrated in vacuo. The residue is partitioned between EtOAc and water, and extracted with EtOAc. The extracts are dried (Na2SO4), and concentrated to afford (6-chloro-2-methoxy-pyrimidin-4-yl)-isochroman-1-ylmethyl-amine (0.84 g). LCMS: RT=2.94 minutes; MS: 306 (M+H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 4 h
  3. concentrationconcentrated in vacuo
  4. customThe residue is partitioned between EtOAc and water
  5. extractionextracted with EtOAc
  6. dry with materialThe extracts are dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3cd611459e61428ebfba335b14970b4e
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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