Sodium Azide → HCID 178478144, compound

HRID 567762Notes

Reaction equation

HRID 567762 reaction equation
[Cl-].[Li+].[N-:3]=[N+:4]=[N-:5].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[NH:11][C:12]1[C:13]2[CH:20]=[C:19]([C:21]#[N:22])[NH:18][C:14]=2[N:15]=[CH:16][N:17]=1>COC(O)C>[Cl:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[NH:11][C:12]1[C:13]2[CH:20]=[C:19]([C:21]3[NH:22][N:5]=[N:4][N:3]=3)[NH:18][C:14]=2[N:15]=[CH:16][N:17]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 212626714-(3-chloroanilino)-6-cyano-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 178478144HCID 178478144, compound

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

19 mg (0.45 mmol) of lithium chloride and 19.5 mg (0.30 mmol) of sodium azide are added to a solution of 80.9 mg (0.30 mmol) of 4-(3-chloroanilino)-6-cyano-7H-pyrrolo[2,3-d]pyrimidine in 1 ml of methoxyethanol and the mixture is heated to boiling for 6.5 h. The cooled reaction mixture is poured onto water/HCl (conc.) 10:1, the mixture is stirred for 30 min, and the solid is filtered off and washed with water. Dissolving the crystals in THF/isopropanol, partial evaporation to crystallization, filtering off and washing with diethyl ether affords 4-(3-chloroanilino)-6-(tetrazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidine; HPLC: tRet(Grad20)=9.5; TLC-Rf=0.45 (CH2Cl2/methanol=7:1); FAB-MS: (M+H)+=313.

Workup

  1. temperaturethe mixture is heated
  2. customThe cooled reaction mixture
  3. additionis poured onto water/HCl (conc.) 10:1
  4. filtrationthe solid is filtered off
  5. washwashed with water
  6. dissolutionDissolving the crystals in THF/isopropanol
  7. custompartial evaporation
  8. customto crystallization
  9. filtrationfiltering off
  10. washwashing with diethyl ether

Sources & evidence

ORD record
ord-4a32adf7898342d19beaead2f5b419d7
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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