Water → N4-[2-(tert-butylcarbonyl)amino-3-methoxypyrid-6-yl]-2-chloro-5-fluoro-4-pyrimidineamine

HRID 2408394Notes

Reaction equation

HRID 2408394 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[C:5]([O:15][CH3:16])=[CH:4][CH:3]=1.[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([F:25])=[CH:20][N:19]=1.O>CO>[C:11]([C:9]([NH:8][C:6]1[C:5]([O:15][CH3:16])=[CH:4][CH:3]=[C:2]([NH:1][C:20]2[C:21]([F:25])=[CH:22][N:23]=[C:18]([Cl:17])[N:19]=2)[N:7]=1)=[O:10])([CH3:13])([CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 962Water2×HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 575629536-Amino-2-(tert-butylcarbonyl)amino-3-methoxypyridine

Product 1

HCID 57562886N4-[2-(tert-butylcarbonyl)amino-3-methoxypyrid-6-yl]-2-chloro-5-fluoro-4-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A homogeneous mixture of 6-amino-2-(tert-butylcarbonyl)amino-3-methoxypyridine (35) (1.5 g, 6.72 mmol) and 2,4-dichloro-5-fluoropyrimidine (53) (1.68 g, 10 mmol) in methanol:water (20 mL, each) was stirred at 60° C. for 48 hours. The reaction mixture upon dilution with water (100 mL) gave a solid, which was isolated by filtration to obtain N4-[2-(tert-butylcarbonyl)amino-3-methoxypyrid-6-yl]-2-chloro-5-fluoro-4-pyrimidineamine. LCMS: purity: 89%; MS (m/z): 354 (MH+).

Workup

  1. customwhich was isolated by filtration

Sources & evidence

ORD record
ord-8f74d827958640b2b5f3d64efe6f74f2
Source dataset
uspto-grants-2014_08
Patent number
US08815848B2

Reaction notes

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