Water → HCID 23151276, compound

HRID 2386965Notes

Reaction equation

HRID 2386965 reaction equation
[Cl:1][C:2]1[N:31]=[CH:30][C:5]2[N:6]=[C:7]([CH3:29])[N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:13][C:12]=3[O:27]C)[C:9](=[O:10])[C:4]=2[CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[N:31]=[CH:30][C:5]2[N:6]=[C:7]([CH3:29])[N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:13][C:12]=3[OH:27])[C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 23151385HCID 23151385, compound

Product 1

HCID 23151276HCID 23151276, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-chloro-3-[2-methoxy-4-(3-piperidin-1-ylpropoxy)phenyl]-2-methylpyrido[3,4-d]pyrimidin-4(3H)-one synthesized in Example 184 (143 mg, 0.32 mmol) was dissolved in methylene chloride (3 mL), boron tribromide (1M methylene chloride solution, 3.2 mmol) was added on an ice bath, stirred at room temperature for 15 hours, and stirred at 40° C. for 3 hours. Saturated carbonated water was added to stop the reaction, the mixture was extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The product was purified by silica gel column chromatography (chloroform/methanol=20/1), and the target compound (49 mg, 35%) was obtained as a light yellow solid.

Workup

  1. stirringstirred at 40° C. for 3 hours
  2. additionwas added
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe product was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-b6b19e23b7694fd0b2b1d5607b765a4f
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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