2,4-Dichloro-5-fluoropyrimidine → HCID 86641891, compound

HRID 880527Notes

Reaction equation

HRID 880527 reaction equation
[NH2:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[N:5]([CH3:10])[C:4]([CH3:12])([CH3:11])[CH2:3]1.[Cl:13][C:14]1[N:19]=[CH:18][C:17]([F:20])=[C:16](Cl)[N:15]=1>CO>[ClH:13].[Cl:13][C:14]1[N:19]=[C:18]([NH:1][CH:2]2[CH2:3][C:4]([CH3:12])([CH3:11])[N:5]([CH3:10])[C:6]([CH3:8])([CH3:9])[CH2:7]2)[C:17]([F:20])=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidine

Product 1

HCID 86641891HCID 86641891, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Amino-1,2,2,6,6-pentamethylpiperidine (1 g) and 2,6-dichloro-5-fluoropyrimidine (1.5 g) were dissolved in methanol (10 mL). The reaction solution was stirred at rt overnight. The reaction solution was evaporated and crystallized from ethyl acetate and hexanes to give 2-chloro-5-fluoro-N4-(1,2,2,6,6-pentamethylpiperidin-4-yl)-4-pyrimidineamine HCl salt (1.65 g, 93%). 1H NMR (DMSO-d6): δ 1.38 (s, 6H), 1.48 (s, 6H), 2.02 (m, 4H), 2.68 (d, J=4.8 Hz, 3H), 4.33 (br, 1H), 8.10 (d, J=3.3 Hz, 1H), 8.32 (d, J=6.9 Hz, 1H), 9.66 (br, 1H).

Workup

  1. customThe reaction solution was evaporated
  2. customcrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-dc70e9466a9b4b08a29a20887f5d371b
Source dataset
uspto-grants-2015_03
Patent number
US08993585B2

Reaction notes

Loading…