Carbonic acid-guanidine (1:1) → 2,4-Quinazolinediamine, 5-iodo-

HRID 1364386Notes

Reaction equation

HRID 1364386 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[C:4]#[N:5].C(=O)(O)O.[NH2:15][C:16]([NH2:18])=[NH:17]>CC(N(C)C)=O>[I:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]2[C:3]=1[C:4]([NH2:5])=[N:17][C:16]([NH2:18])=[N:15]2

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 5227222-Fluoro-6-iodobenzonitrile

Product 1

HCID 1987102,4-Quinazolinediamine, 5-iodo-Yield 19.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
165 °C

Procedure

2-Fluoro-6-iodobenzonitrile (700 mg; 2.83 mmol) is dissolved in dimethylacetamide (5 mL) with guanidine carbonate (766 mg; 4.25 mmol). The vessel is purged with N2, sealed, and heated to 165° C. for 5 hours. After cooling to room temperature, the reaction mixture is placed in the freezer overnight. The precipitate which has formed is removed by filtration and purified by recrystallization from 50% EtOH/water. The resulting solids are filtered and dried at room temperature to yield 158 mg of 5-iodoquinazoline-2,4-diamine.

Workup

  1. customThe vessel is purged with N2
  2. customsealed
  3. temperatureAfter cooling to room temperature
  4. customis placed in the freezer overnight
  5. customThe precipitate which has formed
  6. customis removed by filtration
  7. custompurified by recrystallization from 50% EtOH/water
  8. filtrationThe resulting solids are filtered
  9. customdried at room temperature

Sources & evidence

ORD record
ord-fd80cfb05a274f59825c448c1b8af776
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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