Dimethylacetamide → 7-Fluoroquinazolin-2-amine

HRID 2244088Notes

Reaction equation

HRID 2244088 reaction equation
F[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(=O)(O)O.[NH2:15][C:16]([NH2:18])=[NH:17].C(N(CC)C(C)C)(C)C.CN(C)C(=O)C>C(OCC)(=O)C.O>[F:10][C:8]1[CH:9]=[C:2]2[C:3]([CH:4]=[N:15][C:16]([NH2:18])=[N:17]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 737702,4-DifluorobenzaldehydeHCID 81531DiisopropylethylamineHCID 286947Carbonic acid-guanidine (1:1)

Product 1

HCID 104872107-Fluoroquinazolin-2-amineYield 19.4%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

2,4-difluorobenzaldehyde (4.26 g, 30 mmol), guanidine carbonate (5.40 g, 30 mmol), N,N-diisopropylethylamine (3.87 g, 30 mmol), and N,N-dimethylacetamide (25 mL) are heated at 160 degrees Celsius overnight. The crude product is taken up in ethyl acetate/water. The organic layer is dried over magnesium sulfate, then concentrated and subjected to chromatography, affording the desired 7-fluoroquinazolin-2-amine (0.95 g, 19%). LC/MS m/z=164 [M+H]+.

Workup

  1. dry with materialThe organic layer is dried over magnesium sulfate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0bc23107343343ddbb7257595d372df5
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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