Phosphorus tribromide → HCID 71765539, compound

HRID 2272967Notes

Reaction equation

HRID 2272967 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:19])[C:11]3[N:12]([N:14]=[C:15]([CH2:17]O)[CH:16]=3)[CH:13]=2)=[CH:4][CH:3]=1.P(Br)(Br)[Br:21]>ClCCl>[Br:21][CH2:17][C:15]1[CH:16]=[C:11]2[C:10](=[O:19])[NH:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[CH:13][N:12]2[N:14]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 89826269HCID 89826269, compound

Product 1

HCID 71765539HCID 71765539, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 142 mg (0.445 mmol) 6-(4-bromo-phenyl)-2-hydroxymethyl-5H-pyrazolo[1,5-a]pyrazin-4-one in 8 ml dichloromethane is added 52 μl (0.56 mmol) phosphorus tribromide. The reaction mixture is stirred for 20 hours at room temperature. The mixture is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated. Purification by preparative HPLC (RP18 silica gel, eluent water/acetonitrile/formic acid) affords 2-bromomethyl-6-(4-bromo-phenyl)-5H-pyrazolo[1,5-a]pyrazin-4-one as off-white solid; HPLC/MS 2.21 min (A), [M+H] 384.

Workup

  1. customThe mixture is partitioned between water and dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customPurification by preparative HPLC (RP18 silica gel, eluent water/acetonitrile/formic acid)

Sources & evidence

ORD record
ord-dafa7821669a4e22a8a0fa338ae8602b
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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