Diisopropylethylamine → HCID 178482927, compound

HRID 415435Notes

Reaction equation

HRID 415435 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][N:11]([CH3:18])[C:12]1[NH:16][N:15]=[C:14]([NH2:17])[CH:13]=1.CCN(C(C)C)C(C)C>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][C:14]2[CH:13]=[C:12]([N:11]([CH3:18])[CH3:10])[NH:16][N:15]=2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 178482959HCID 178482959, compound

Product 1

HCID 178482927HCID 178482927, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-dichloro-5-fluoropyrimidine (166 mg, 1 mmol), N5,N5-dimethyl-1H-pyrazole-3,5-diamine (Method 34, 150 mg, 1.2 mmol), and DIEA (0.35 ml, 2 mmol) in ethanol (3 ml) was heated at 55° C. overnight. Solvent was removed, and the residue was purified by silica gel chromatography (by ISCO Combiflash with a gradient of 0-5% methanol in methylene chloride with 1% NH4OH). 100 mg product was obtained as a white solid (40%). MS: 257 (M+1); NMR (DMSO-d6, 400 MHz, 80° C.) δ11.60 (br, 1H), 10.26 (br, 1H), 8.23 (s, 1H), 5.73 (s, 1H), 2.76 (s, 6H).

Workup

  1. customSolvent was removed
  2. customthe residue was purified by silica gel chromatography (by ISCO Combiflash with a gradient of 0-5% methanol in methylene chloride with 1% NH4OH)

Sources & evidence

ORD record
ord-4e47db7c8a5946159acb41d43c4e18e5
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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