Water → HCID 59186792, compound

HRID 1921909Notes

Reaction equation

HRID 1921909 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]=[C:11](O)[CH:10]=[CH:9][N:8]=2)=[CH:3][CH:2]=1.P(Br)(Br)([Br:16])=O.O.C(Cl)Cl>ClCCCl>[Br:16][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24613Phosphorus oxybromideHCID 178516492HCID 178516492, compound

Product 1

HCID 59186792HCID 59186792, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
95 °C

Procedure

2-Pyridin-4-yl-pyrimidin-4-ol (200 mg, 1.16 mmol) was suspended in DCE (10 mL) then POBr3 (497 mg, 1.73 mmol) was added in one portion. The reaction mixture was heated to 95° C. (bath) for 18 h then cooled to 20° C. H2O (30 mL) and CH2Cl2 (30 mL) were added, then the biphasic mixture was stirred vigorously for 30 min. The layers were separated and the aqueous phase was extracted with CH2Cl2 (3×30 mL). The combined organics were evaporated to dryness to afford the title compound: m/z (ES+)=236, 238 (1:1) [M+H]+.

Workup

  1. temperaturethen cooled to 20° C
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (3×30 mL)
  4. customThe combined organics were evaporated to dryness

Sources & evidence

ORD record
ord-b64558471e924489ae7bc84849027077
Source dataset
uspto-grants-2012_05
Patent number
US08173807B2

Reaction notes

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