Ammonium Chloride → 7-Fluoro-pyrido[3,2-d]pyrimidin-4-amine

HRID 2244081Notes

Reaction equation

HRID 2244081 reaction equation
F[C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.C(O)(=O)C.[CH:15]([NH2:17])=[NH:16].CCN(C(C)C)C(C)C.[NH4+].[Cl-]>CC(N(C)C)=O>[F:8][C:6]1[CH:5]=[N:4][C:3]2[C:9]([NH2:10])=[N:17][CH:15]=[N:16][C:2]=2[CH:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 160693Formamidine acetateHCID 27832532-Cyano-3,5-difluoropyridine

Product 1

HCID 250596967-Fluoro-pyrido[3,2-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

3,5-Difluoro-pyridine-2-carbonitrile (2.54 mmol, 356 mg) is dissolved in DMA (5 mL) and then formamidine acetate is added (2.54 mmol, 264.6 mg) followed by DIEA (7.62 mmol, 983 mg). The reaction mixture is stirred for 16 h at 100° C., then poured into saturated NH4Cl aq. and extracted 3 times with CH2Cl2. The organics are dried with Na2SO4, concentrated, and purified on Biotage with 0-20% MeOH in CH2Cl2. This gives the desired product 7-Fluoro-pyrido[3,2-d]pyrimidin-4-ylamine (27 mg, LC/MS m/z=165 [M+H]+) as a white powder.

Workup

  1. extractionextracted 3 times with CH2Cl2
  2. dry with materialThe organics are dried with Na2SO4
  3. concentrationconcentrated
  4. custompurified on Biotage with 0-20% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-e87084a4f3c844bc90ce91b2ed4790ba
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

Loading…