Guanidine Hydrochloride → 2,4-Quinazolinediamine, 7-fluoro-

HRID 2244052Notes

Reaction equation

HRID 2244052 reaction equation
F[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:12][C:13]([NH2:15])=[NH:14].[H-].[Na+].C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[F:10][C:8]1[CH:9]=[C:2]2[C:3]([C:4]([NH2:5])=[N:14][C:13]([NH2:15])=[N:12]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 24758Sodium hydrideHCID 775452,4-DifluorobenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 4562212,4-Quinazolinediamine, 7-fluoro-Yield 28.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

2,4-Difluorobenzonitrile (2.78 g, 1 eq), guanidine hydrochloride (7.15 g, 3.74 eq), and sodium hydride (3.6 g, 7.6 eq) are added to dimethylacetamide (50 mL) and the resulting mixture is stirred at 150° C. for overnight. Then the reaction mixture is poured into sat'd NaHCO3 aq. solution (300 mL), extracted by EtOAc (3×200 mL). The combined organic layers is dried over Na2SO4, filtered, concentrated. The crude product is purified by flash chromatography to give 7-Fluoro-quinazolin-2,4-diamine (1 g, 28% yield). LC/MS m/z=179 [M+H]+.

Workup

  1. extractionextracted by EtOAc (3×200 mL)
  2. dry with materialThe combined organic layers is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-716f646ee36a4670a66b6a7fb9b6f03a
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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