Methylamine → HCID 58075388, compound

HRID 475838Notes

Reaction equation

HRID 475838 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:11][O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.[CH3:24][NH2:25]>CO>[Cl:1][C:2]1[N:3]=[C:4]([NH:25][CH3:24])[C:5]2[CH2:11][O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 58075685HCID 58075685, compound

Product 1

HCID 58075388HCID 58075388, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,4-dichloro-8-(4-(trifluoromethoxy)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (Preparation AB) (80.7 mg, 0.221 mmol) in MeOH (2210 μL) was added methylamine (1000 μL, 2.0 mmol) (2M in THF). The reaction was allowed to stir overnight. Removed the solvent and applied to silica gel, eluting with an EtOAc/Hex gradient to afford 2-chloro-N-methyl-8-(4-(trifluoromethoxy)phenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine (69.8 mg, 0.194 mmol, 88% yield). LC-MS (M+H)+=360.0.

Workup

  1. customRemoved the solvent
  2. washeluting with an EtOAc/Hex gradient

Sources & evidence

ORD record
ord-2bd66951367941c080b822d884cf1569
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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