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

HRID 388239Notes

Reaction equation

HRID 388239 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-f4c97dc1e0a842ab9911efa75767c152
Source dataset
uspto-grants-2013_02
Patent number
US08377924B2

Reaction notes

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