Phosphorus oxychloride → 5-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amine

HRID 1516838Notes

Reaction equation

HRID 1516838 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=O)[C:5]2[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.O=P(Cl)(Cl)[Cl:21]>>[CH2:11]([N:10]1[C:5]2[C:4]([Cl:21])=[N:3][C:2]([NH2:1])=[N:7][C:6]=2[CH:8]=[CH:9]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1359874852-amino-3,5-dihydro-5-benzyl-4H-Pyrrolo[3,2-d]pyrimidin-4-one

Product 1

HCID 576936175-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amineYield 40%

Conditions

Temperature
116 °C

Procedure

A mixture of 2-amino-5-benzyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (1.1 g, 7.4 mmol) and POCl3 (7 mL, 74 mmol) was heated at 116° C. for 3 h. Upon completion of the reaction, the reaction mixture was poured into ice and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by column chromatography, eluting with CH2Cl2/Acetone (3:1), afforded the product as a white solid (490 mg, 40%).

Workup

  1. customUpon completion of the reaction
  2. additionthe reaction mixture was poured into ice
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by column chromatography
  9. washeluting with CH2Cl2/Acetone (3:1)

Sources & evidence

ORD record
ord-bbd6dbecd94f49bd82028e2c9c32f8b0
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Reaction notes

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