(1-Methyl-1H-pyrazol-5-yl)methanamine → HCID 71285373, compound

HRID 536522Notes

Reaction equation

HRID 536522 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=[N:3]1.[F:9][C:10]1[CH:38]=[CH:37][CH:36]=[CH:35][C:11]=1[CH2:12][N:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[C:15]([C:22]2[N:23]=[C:24](I)[C:25]3[C:30]([CH3:32])([CH3:31])[C:29](=[O:33])[NH:28][C:26]=3[N:27]=2)=[N:14]1>CN1CCCC1=O>[F:9][C:10]1[CH:38]=[CH:37][CH:36]=[CH:35][C:11]=1[CH2:12][N:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[C:15]([C:22]2[N:23]=[C:24]([NH:8][CH2:7][C:6]3[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=3)[C:25]3[C:30]([CH3:31])([CH3:32])[C:29](=[O:33])[NH:28][C:26]=3[N:27]=2)=[N:14]1

Participants

4

Reactant 2

HCID 7019421(1-Methyl-1H-pyrazol-5-yl)methanamineHCID 867053672-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Product 1

HCID 71285373HCID 71285373, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

111.1 mg (1.0 mmol) of 1-(1-methyl-1H-pyrazol-5-yl)methanamine was put in a vial of a microwave reactor block and a solution of 51.4 mg (100 μmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (example 15A) in 0.6 ml of 1-methyl-2-pyrrolidinone was added. Then the reactor block was sealed and was irradiated for 6 h with microwaves, in order to reach and maintain a temperature of the mixture of 170° C. After cooling, it was purified by preparative LC-MS (method 6). The product-containing fractions were concentrated by evaporation by means of a centrifugal dryer under vacuum. The residue of the individual fractions was in each case dissolved in 0.6 ml DMSO and combined. Then the solvent was evaporated completely in the centrifugal dryer. 32.7 mg (61% of theor.) of the target product was obtained.

Workup

  1. customThen the reactor block was sealed
  2. customwas irradiated for 6 h with microwaves, in order
  3. temperaturemaintain
  4. additiona temperature of the mixture of 170° C
  5. temperatureAfter cooling
  6. customit was purified by preparative LC-MS (method 6)
  7. concentrationThe product-containing fractions were concentrated by evaporation by means of a centrifugal dryer under vacuum
  8. dissolutiondissolved in 0.6 ml DMSO
  9. customThen the solvent was evaporated completely in the centrifugal dryer
  10. custom32.7 mg (61% of theor.) of the target product was obtained

Sources & evidence

ORD record
ord-57d10c9d7e684d33ae197a28270ce874
Source dataset
uspto-grants-2014_10
Patent number
US08859569B2

Reaction notes

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