Water → 7-Chloro-5-fluoroquinazolin-2-amine

HRID 715071Notes

Reaction equation

HRID 715071 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.C(=O)(O)O.C(=O)(O)O.[NH2:20][C:21]([NH2:23])=[NH:22].O>CC(N(C)C)=O>[Cl:1][C:2]1[CH:9]=[C:8]2[C:5]([CH:6]=[N:20][C:21]([NH2:23])=[N:22]2)=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27735124-Chloro-2,6-difluorobenzaldehydeHCID 13000414Guanidine bis(carbonate)

Product 1

HCID 894019697-Chloro-5-fluoroquinazolin-2-amineYield 63%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred suspension of 4-chloro-2,6-difluorobenzaldehyde (45 g, 255 mmol) in DMA (360 mL), at room temperature under nitrogen was added guanidine bis(carbonate) (70.0 g, 382 mmol). The mixture was heated to 140° C. for 3 hours. The reaction was then cooled to room temperature followed by addition of 400 mL water with stirring. The mixture was then filtered. The solids were then collected and triturated in 200 mL methanol for 10 minutes, then filtered. These solids were then dried in vacuo to obtain 31.6 g (63%) of 7-chloro-5-fluoroquinazolin-2-amine (82a) as a brown solid.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. filtrationThe mixture was then filtered
  3. customThe solids were then collected
  4. customtriturated in 200 mL methanol for 10 minutes
  5. filtrationfiltered
  6. customThese solids were then dried in vacuo

Sources & evidence

ORD record
ord-01a889f820ed4a8c8dea36f3887f40c6
Source dataset
uspto-grants-2015_11
Patent number
US09187462B2

Reaction notes

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