Hydrogen Bromide → HCID 71245087, compound

HRID 574001Notes

Reaction equation

HRID 574001 reaction equation
[Cl:1][C:2]1[C:3]([NH:17][C@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=2)[CH3:19])=[N:4][C:5]([NH:8][C:9]2[C:10]([O:15]C)=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.Br>>[Cl:1][C:2]1[C:3]([NH:17][C@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=2)[CH3:19])=[N:4][C:5]([NH:8][C:9]2[C:10](=[O:15])[NH:11][CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 71247459HCID 71247459, compound

Product 1

HCID 71245087HCID 71245087, compoundYield 91%

Conditions

Temperature
100 °C

Procedure

A mixture of (S)-5-chloro-N4-(1-(5-fluoropyridin-2-yl)ethyl)-N2-(2-methoxypyridin-3-yl) pyrimidine-2,4-diamine (Preparation 3b, 0.184 g, 0.49 mmol) and 48% aqueous hydrogen bromide solution (1.6 mL) was heated to 100° C. for 3 hours. 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). The combined organic extracts were dried (Na2SO4) and the solvent evaporated to yield the title compound (0.154 g, 91%) as a white solid.

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. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-2d8139e5884d40b38f6ce8dcaf537886
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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