Hydrogen Bromide → 2-Anilino-4-hydroxypyrimidine

HRID 2241231Notes

Reaction equation

HRID 2241231 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:4]=1.Br.[OH-].[Na+]>C(O)(=O)C.O>[C:10]1([NH:9][C:5]2[NH:4][C:3](=[O:2])[CH:8]=[CH:7][N:6]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 156155044-methoxy-N-phenylpyrimidin-2-amine

Product 1

HCID 14038522-Anilino-4-hydroxypyrimidineYield 94.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
92.5 °C

Procedure

To a solution of 4-methoxy-N-phenylpyrimidin-2-amine (0.632 g, 3.14 mmol) in acetic acid (20 mL) was added HBr (2.132 mL, 18.84 mmol; 48 wt % in H2O). The reaction mixture was stirred at 90-95° C. for 3 hours. The reaction mixture was cooled to room temperature and diluted with H2O. The pH of the reaction mixture was adjusted to 5-6 with 6 M aqueous NaOH which resulted in the formation of a solid precipitate. The solid was filtered, washed with H2O, collected and dried under vacuum to yield the desired product (0.553 g, 94%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.74 (br s, 1H), 8.81 (br s, 1H), 7.76 (s, 1H), 7.60 (d, J=7.8 Hz, 2H), 7.31 (t, J=8.0 Hz, 2H), 7.02 (t, J=7.4 Hz, 1H), 5.81 (s, 1H). LRMS (ESI pos) m/e 188 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customresulted in the formation of a solid precipitate
  3. filtrationThe solid was filtered
  4. washwashed with H2O
  5. customcollected
  6. customdried under vacuum

Sources & evidence

ORD record
ord-11ebbc6d30874666b7516bb3c20ca502
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

Loading…