Phosphorus oxybromide → HCID 57929477, compound

HRID 2386663Notes

Reaction equation

HRID 2386663 reaction equation
P(Br)(Br)([Br:3])=O.[CH:6]1([N:11]2[C:16]3[N:17]=[C:18]([S:21][CH3:22])[N:19]=[CH:20][C:15]=3[C:14](O)=[CH:13][C:12]2=[O:24])[CH2:10][CH2:9][CH2:8][CH2:7]1>ClC(Cl)C>[Br:3][C:14]1[C:15]2[CH:20]=[N:19][C:18]([S:21][CH3:22])=[N:17][C:16]=2[N:11]([CH:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[C:12](=[O:24])[CH:13]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 57929480HCID 57929480, compound

Product 1

HCID 57929477HCID 57929477, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorus oxybromide (11.3 mL) was added to a mixture of 8-cyclopentyl-5-hydroxy-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (2.56 g, 9.23 mmol) in dichloro-ethane (13 mL) at RT. The reaction mixture was heated to 100° C. in a microwave reactor for 1 h, then cooled to RT. The resulting mixture was partitioned between EtOAc (200 mL) and NaHCO3 (sat'd aq, 200 mL), and the aqueous layer extracted with EtOAc (100 mL). The combined organic layers were washed with NaHCO3 (sat'd aq, 3×100 mL) and water (2×100 mL), dried over MgSO4, filtered and evaporated under reduced pressure to give 1.58 g (50% yield) of 5-bromo-8-cyclopentyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one. MS=340, 342 [M+H]+.

Workup

  1. temperaturecooled to RT
  2. customThe resulting mixture was partitioned between EtOAc (200 mL) and NaHCO3 (sat'd aq, 200 mL)
  3. extractionthe aqueous layer extracted with EtOAc (100 mL)
  4. washThe combined organic layers were washed with NaHCO3 (sat'd aq, 3×100 mL) and water (2×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8efa336ff8b54872bcb92d058b3c099d
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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