N-Methylethylamine → 2-chloro-N-ethyl-N-methyl-8-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine

HRID 475777Notes

Reaction equation

HRID 475777 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][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.[CH3:19][NH:20][CH2:21][CH3:22]>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:20]([CH2:21][CH3:22])[CH3:19])[C:5]2[CH2:11][O:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 12219N-MethylethylamineHCID 580755292,4-Dichloro-8-phenyl-7,8-dihydro-5H-pyrano[4,3-D]pyrimidine

Product 1

HCID 580756272-chloro-N-ethyl-N-methyl-8-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amineYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,4-dichloro-8-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (135 mg, 0.480 mmol) and excess N-methylethanamine (284 mg, 4.80 mmol) in MeOH (2 mL) was stirred at rt for 1 h. The solvent was removed in vacuum to afford 2-chloro-N-ethyl-N-methyl-8-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine (146 mg, 0.481 mmol, 100% yield). LC-MS (M+H)+=304.2.

Workup

  1. customThe solvent was removed in vacuum

Sources & evidence

ORD record
ord-1da7bba1b30241f7896e5fdab695d21b
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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