Hydrogen Bromide → HCID 71498512, compound

HRID 574002Notes

Reaction equation

HRID 574002 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[C:16]([O:17]C)=[CH:15][N:14]=[C:13]([NH:19][C:20]3[C:21]([O:26]C)=[N:22][CH:23]=[CH:24][CH:25]=3)[N:12]=2)[CH3:9])=[N:6][CH:7]=1.Br>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[C:16]([OH:17])=[CH:15][N:14]=[C:13]([NH:19][C:20]3[C:21](=[O:26])[NH:22][CH:23]=[CH:24][CH:25]=3)[N:12]=2)[CH3:9])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 90409437HCID 90409437, compound

Product 1

HCID 71498512HCID 71498512, compoundYield 25.4%

Conditions

Temperature
100 °C

Procedure

A mixture of (S)—N4-(1-(5-fluoropyridin-2-yl)ethyl)-5-methoxy-N2-(2-methoxypyridin-3-yl)pyrimidine-2,4-diamine (Preparation 4b, 0.200 g, 0.54 mmol) and 48% aqueous hydrogen bromide solution (1.8 mL) was stirred and heated to 100° C. overnight. The solvent was evaporated under reduced pressure and the residue was treated with a saturated aqueous solution of potassium carbonate and then extracted with ethyl acetate (×3). Concentrated aqueous hydrogen chloride solution was then added to the aqueous solution until an acidic pH was reached and the white solid that formed was filtered and dried to give the title compound (0.047 g, 25%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was treated with a saturated aqueous solution of potassium carbonate
  3. extractionextracted with ethyl acetate (×3)
  4. additionConcentrated aqueous hydrogen chloride solution was then added to the aqueous solution until an acidic pH
  5. customthe white solid that formed
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-185b45e6aa8f4da58f1024f363ddbb4e
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

Loading…