Ethylamine → HCID 58075546, compound

HRID 2370189Notes

Reaction equation

HRID 2370189 reaction equation
[CH2:1]([NH2:3])[CH3:2].[Cl:4][C:5]1[N:6]=[C:7](Cl)[C:8]2[CH2:14][O:13][CH2:12][CH:11]([C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=3)[C:9]=2[N:10]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:4][C:5]1[N:6]=[C:7]([NH:3][CH2:1][CH3:2])[C:8]2[CH2:14][O:13][CH2:12][CH:11]([C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=3)[C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 58075759HCID 58075759, compound

Product 1

HCID 58075546HCID 58075546, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of ethanamine (406 μL, 0.812 mmol), 2,4-dichloro-8-(3,5-difluorophenyl)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (Preparation X) (117 mg, 0.369 mmol) and DIEA (161 μL, 0.922 mmol) in THF (1845 μL) was stirred at RT for 2 h. The mixture was concentrated and purified by column chromatography on silica gel to give 2-chloro-8-(3,5-difluorophenyl)-N-ethyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine (104 mg, 0.319 mmol, 87% yield). LC-MS (M+H)+=326.1.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-40abfc5d99f9433caa0250c31468ce2b
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

Loading…