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

HRID 1746153Notes

Reaction equation

HRID 1746153 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-06b258f8a38141abb03dbad3a4196561
Source dataset
uspto-grants-2015_10
Patent number
US09149475B2

Reaction notes

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