Triethylamine → 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine

HRID 1042266Notes

Reaction equation

HRID 1042266 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[C:10]([CH:11]=O)=[C:9](Cl)[N:8]=[CH:7][N:6]=1.[N+](C)([O-])=O.C(=O)=O.C(N(CC)CC)C>CO>[Cl:4][C:5]1[N:6]=[CH:7][N:8]=[C:9]2[NH:2][N:3]=[CH:11][C:10]=12

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 8196914,6-Dichloro-5-pyrimidinecarbaldehydeHCID 86649311HCID 86649311, compound

Product 1

HCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidineYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine hydrate (2.0 ml, 41 mmol) was slowly added to a solution of 4,6-dichloropyrimidine-5-carbaldehyde (7.2 g, 41 mmol) in MeOH (150 ml)-60° C. (nitromethane-dry ice bath) followed by triethylamine (6.8 mL, 49 mmol). The mixture was allowed to warm to rt and stirred for 2 h. MeOH was removed in vacuo and water (150 mL) was added. The mixture was extracted with EtOAc (3×80 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, and filtered through a glass funnel. Removal of solvent gave 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (4.45 g, 71%). MS (ESI, pos. ion) m/z: 155 [M+H]+

Workup

  1. customMeOH was removed in vacuo and water (150 mL)
  2. additionwas added
  3. extractionThe mixture was extracted with EtOAc (3×80 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered through a glass funnel
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-3e968d1cc01a42aeb4cf26f5ec208e55
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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