Ammonium formate → HCID 12041006, compound

HRID 1241459Notes

Reaction equation

HRID 1241459 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)[N:5]=[C:4]([NH2:25])[C:3]=1[N:26]1[CH2:30][CH2:29][CH2:28][S:27]1(=[O:32])=[O:31].C([O-])=O.[NH4+]>CO.[Pd]>[O:32]=[S:27]1(=[O:31])[CH2:28][CH2:29][CH2:30][N:26]1[C:3]1[C:4]([NH2:25])=[N:5][C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)=[N:7][CH:2]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 9912738HCID 9912738, compound

Product 1

HCID 12041006HCID 12041006, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Alternatively, 5-(1,1-dioxido-2-isothiazolidinyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-pyrimidinylamine (example 2) was prepared from 6-chloro-5(1,1-dioxido-2-isothiazolidinyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3yl]-4-pyrimidineamine (0.040 mg, 0.084 mmol) from example 1, which was dissolved in MeOH (4 ml) and to which Pd/C (10%, 0.009 g) and ammonium formate (0.053 mg, 0.84 mmol, 10 equivalents) were added. The mixture was heated under reflux for 2 days and then allowed to cool to room temperature, before the catalyst was filtered off. The crude product was concentrated in vacuo.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 days
  4. filtrationwas filtered off
  5. concentrationThe crude product was concentrated in vacuo

Sources & evidence

ORD record
ord-21f78a87c36d41f89f2284c26bf76393
Source dataset
uspto-grants-2006_10
Patent number
US07115599B2

Reaction notes

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