Hydrochloric Acid → HCID 21883104, compound

HRID 722248Notes

Reaction equation

HRID 722248 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=O)[C:5]2[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][NH:8][C:6]=2[N:7]=1.C(OC(=O)C)(=O)C.C1(N(C)C)C=CC=CC=1.O=P(Cl)(Cl)[Cl:33].Cl>CC#N>[Cl:33][C:4]1[C:5]2[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][NH:8][C:6]=2[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 7918Acetic AnhydrideHCID 24813Phosphorus oxychlorideHCID 135839363HCID 135839363, compound

Product 1

HCID 21883104HCID 21883104, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-amino-5-isopropyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one and acetic anhydride (20 mL) was heated to reflux for 3 h and evaporated. The residue was treated with BnNEt3Cl (8.99 g, 40 mmol), PhNMe2 (4.9 mL) and POCl3 (17 mL, 120 mmol) in CH3CN (100 mL) at 100° C. for 40 min and concentrated. The residue was poured into ice water and neutralized with 2N NaOH, extracted with EtOAc (80 mL×3), and evaporated to give an oil which was digested with methanolic 4N HCl (50 mL) at 50° C. for 2 h. After cooling, and neutralization to pH 7 with 2N NaOH, the solid was collected by filtration and dried to give 4-chloro-5-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine (1.88 g, 45%). HPLC Rt: 5.796 min. 1H-NMR (DMSO-d6): δ 11.170 (s, 1H), 6.82 (s, 1H), 6.42 (s, 2H), 3.24 (7, 1H), 1.25 (s, 3H), 1.23 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customevaporated
  4. concentrationconcentrated
  5. additionThe residue was poured into ice water and neutralized with 2N NaOH
  6. extractionextracted with EtOAc (80 mL×3)
  7. customevaporated
  8. customto give an oil which
  9. temperatureAfter cooling
  10. filtrationneutralization to pH 7 with 2N NaOH, the solid was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-2d1a8157cf9247009859104ab3a18c72
Source dataset
uspto-grants-2006_11
Patent number
US07138402B2

Reaction notes

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