Benzoyl chloride → HCID 67520551, compound

HRID 1925964Notes

Reaction equation

HRID 1925964 reaction equation
[O:1]([C:8]1[C:9]2[NH:16][C:15](/[CH:17]=[CH:18]/[CH2:19][OH:20])=[CH:14][C:10]=2[N:11]=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1.C(OCC)(=O)C>[C:28]([O:20][CH2:19]/[CH:18]=[CH:17]/[C:15]1[NH:16][C:9]2[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:13][CH:12]=[N:11][C:10]=2[CH:14]=1)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67520665HCID 67520665, compound

Product 1

HCID 67520551HCID 67520551, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2E)-3-(4-Phenoxy-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-2-propen-1-ol (1.0 g) was suspended in tetrahydrofuran (20 mL), and triethylamine (0.651 mL) and benzoyl chloride (0.86 mL) were sequentially added under ice-cooling. The mixture was stirred under ice-cooling for 2 hrs, diluted with ethyl acetate (200 mL) and washed with water (50 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by basic silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→0:100) to give the title compound (1.08 g) as crystals.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hrs
  3. washwashed with water (50 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified by basic silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→0:100)

Sources & evidence

ORD record
ord-4bba910be1d24db3b997e776bfcddf5d
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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