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

HRID 1805859Notes

Reaction equation

HRID 1805859 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-079e7f79be30490ebebef3b2bff402ec
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

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