Ammonia → 5-[4-amino-2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-6-oxo-6,7-dihydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-1-methyl-1H-pyrrole-3-carbonitrile

HRID 2222236Notes

Reaction equation

HRID 2222236 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[CH2:12][N:13]1[C:21]([C:22]2[N:26]([CH3:27])[CH:25]=[C:24]([C:28]#[N:29])[CH:23]=2)=[C:20]2[C:15]([N:16]([CH2:32][CH:33]3[CH2:35][CH2:34]3)[C:17](=[O:31])[NH:18][C:19]2=S)=[N:14]1.[NH3:36]>C1COCC1.CO.[Hg](Cl)Cl>[NH2:36][C:19]1[C:20]2[C:15](=[N:14][N:13]([CH2:12][C:5]3[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=4)[N:8]=[CH:7][CH:6]=3)[C:21]=2[C:22]2[N:26]([CH3:27])[CH:25]=[C:24]([C:28]#[N:29])[CH:23]=2)[N:16]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:17](=[O:31])[N:18]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 100289915-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-6-oxo-4-thioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-1-methyl-1H-pyrrole-3-carbonitrile

Product 1

HCID 104354585-[4-amino-2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-6-oxo-6,7-dihydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-1-methyl-1H-pyrrole-3-carbonitrileYield 48%

Reagents, catalysts & solvents 3

HCID 24085Mercuric ChlorideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

5-[2-[(6-chloroquinolin-4-yl)methyl]-7-(cyclopropylmethyl)-6-oxo-4-thioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-1-methyl-1H-pyrrole-3-carbonitrile (0.5g, 1.0 mmol) was dissolved in 10 mL anhydrous THF. Anhydrous ammonia in methanol (20 mL of 2M solution) was added, followed by mercury (II) chloride (410 mg, 1.5 mmol, 1.5 eq). The mixture was heated to 60° C. for 48 h. Volatiles were evaporated and the residue dissolved in 100 mL ethyl acetate, 50 mL dichloromethane, and 100 mL water. The organic layer was washed with water (100 mL) and dried over sodium sulfate. The residue was purified by chromatography on silica (gradient: dichloromethane to 10% methanol in dichloromethane), yielding 232 mg (48%) of the product as a yellow solid. ES M+H+=485.

Workup

  1. customVolatiles were evaporated
  2. dissolutionthe residue dissolved in 100 mL ethyl acetate
  3. washThe organic layer was washed with water (100 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe residue was purified by chromatography on silica (gradient: dichloromethane to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-962ba727d1db424c8eb129cd0c7a7923
Source dataset
uspto-grants-2008_05
Patent number
US07371757B2

Reaction notes

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