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

HRID 2241233Notes

Reaction equation

HRID 2241233 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]=[C:3]1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CO.[Br:18]Br>C(Cl)(Cl)Cl>[Br:18][C:6]1[C:7](=[O:8])[N:2]([CH3:1])[C:3]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 685179403-methyl-2-(phenylamino)pyrimidin-4(3H)-one

Product 1

HCID 673454265-bromo-3-methyl-2-(phenylamino)pyrimidin-4(3H)-oneYield 100.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (0.104 g, 0.517 mmol) in CHCl3 (5 mL)/MeOH (1 mL) at 0° C. was added bromine (0.027 mL, 0.517 mmol). The reaction mixture was stirred for 30 minutes at room temperature and then quenched with 10% aqueous sodium bisulfite solution. The reaction mixture was partitioned between EtOAc and H2O. The phases were separated, and the aqueous phase was re-extracted with EtOAc (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield the desired product (0.145 g; 100%) as a white solid that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.95 (s, 1H), 7.94 (s, 1H), 7.47 (m, 2H), 7.34 (t, J=7.4 Hz, 2H), 7.14 (t, J=7.4 Hz, 1H), 3.53 (s, 3H). LRMS (ESI pos) m/e 280, 282 (M+1, Br pattern).

Workup

  1. customquenched with 10% aqueous sodium bisulfite solution
  2. customThe reaction mixture was partitioned between EtOAc and H2O
  3. customThe phases were separated
  4. extractionthe aqueous phase was re-extracted with EtOAc (1×)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a7a3d9e8fe1a4c118242eb7f47d23d9d
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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