4-Chloro-6-(morpholin-4-yl)pyrimidin-2-amine → HCID 58504732, compound

HRID 2367205Notes

Reaction equation

HRID 2367205 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([F:10])[C:7]=1[CH:8]=[O:9].Cl[C:15]1[CH:20]=[C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:18]=[C:17]([NH2:27])[N:16]=1>>[NH2:27][C:17]1[N:16]=[C:15]([C:4]2[CH:3]=[C:2]([F:1])[C:7]([CH:8]=[O:9])=[C:6]([F:10])[CH:5]=2)[CH:20]=[C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:18]=1

Participants

3

Reactant 2

HCID 14842884-Chloro-6-(morpholin-4-yl)pyrimidin-2-amineHCID 162177083,5-Difluoro-4-formylphenylboronic acid

Product 1

HCID 58504732HCID 58504732, compoundYield 68%

Procedure

The title compound was prepared following the General Procedure A using: (3,5-difluoro-4-formylphenyl)boronic acid (2.17 g, 11.7 mmol) and 4-chloro-6-(4-morpholinyl)-2-pyrimidinamine (2.50 g, 11.7 mmol). The solid was dry loaded in 10 g of SiO2. Flash chromatography on SiO2 eluting from 100% CHCl3 to 90:10 CHCl3:CH3OH afforded the title compound (2.55 g, 51%) as a yellow solid. LC-MS (ES) m/z=321 [M+H]+.

Workup

  1. customThe title compound was prepared
  2. customThe solid was dry

Sources & evidence

ORD record
ord-f7ae3c7975a24d5c9691d5eb05c2d0c3
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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