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Phosphorus oxychloride → 4-chloro-6-(furan-2-yl)-5H-pyrrolo[3,2-d]pyrimidine

HRID 1786932
Notes
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Reaction equation

HRID 1786932 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:14][C:13]2[C:12](=O)[NH:11][CH:10]=[N:9][C:8]=2[CH:7]=1.P(Cl)(Cl)([Cl:18])=O>O1CCOCC1>[Cl:18][C:12]1[C:13]2[NH:14][C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][C:8]=2[N:9]=[CH:10][N:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1357417756-(furan-2-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-ol

Product 1

HCID 713033474-chloro-6-(furan-2-yl)-5H-pyrrolo[3,2-d]pyrimidineYield 91.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(2-furyl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-4-one (2.20 g) and phosphoryl chloride (10.7 g) was stirred at 100° C. for 20 min, dioxane (30 mL) was added, and the mixture was stirred at 100° C. for 3 hrs. After concentration under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate-acetone (155 mL×4). The organic layers were combined, washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue washed with ethyl acetate-diethyl ether, and dried under reduced pressure at 60° C. to give the title compound (2.19 g).

Workup

  1. stirringthe mixture was stirred at 100° C. for 3 hrs
  2. concentrationAfter concentration under reduced pressure, saturated aqueous sodium hydrogen carbonate
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate-acetone (155 mL×4)
  5. washwashed with saturated brine (100 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe residue washed with ethyl acetate-diethyl ether
  9. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-60364eed59cf42df9902b300bf8ffe2b
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07507740B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes