Methanol → 5-bromo-2-(phenylamino)pyrimidin-4(3H)-one

HRID 1676389Notes

Reaction equation

HRID 1676389 reaction equation
[C:1]1([NH:7][C:8]2[NH:13][C:12](=[O:14])[CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[Br:17]Br>C(Cl)(Cl)Cl.O>[Br:17][C:11]1[C:12](=[O:14])[NH:13][C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:9][CH:10]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 14038522-Anilino-4-hydroxypyrimidine

Product 1

HCID 593534425-bromo-2-(phenylamino)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of 2-(phenylamino)pyrimidin-4(3H)-one (0.200 g, 1.07 mmol) in CHCl3 (5 mL) and a small amount of MeOH at 0° C. was added bromine (0.0547 ml, 1.07 mmol). The reaction was stirred for 40 minutes, diluted with H2O, and then quenched with 10% sodium bisulfite solution. The reaction mixture was diluted with EtOAc, the layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The product was obtained (0.284 g; 100%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 11.32 (br s, 1H), 8.89 (br s, 1H), 8.04 (s, 1H), 7.55 (d, 2H), 7.33 (m, 2H), 7.06 (t, 1H). LRMS (ESI pos) m/e 266, 268 (M+, Br pattern).

Workup

  1. customquenched with 10% sodium bisulfite solution
  2. additionThe reaction mixture was diluted with EtOAc
  3. customthe layers were separated
  4. extractionthe aqueous layer was re-extracted with EtOAc (1×)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was obtained (0.284 g; 100%) as a white solid

Sources & evidence

ORD record
ord-e777dc3bb0714183aeaed243aab4cee7
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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