Potassium Carbonate → HCID 24905198, compound

HRID 238025Notes

Reaction equation

HRID 238025 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([CH:18]([CH3:20])[CH3:19])[N:9]=2)=[CH:4][C:3]=1[O:21][CH3:22].C([O-])([O-])=O.[K+].[K+].Br[CH2:30][CH2:31][CH2:32][OH:33]>CN(C=O)C>[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([CH:18]([CH3:19])[CH3:20])[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][CH:31]([CH3:30])[CH2:32][OH:33])=[C:3]([O:21][CH3:22])[CH:4]=3)[C:16]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 24905251HCID 24905251, compound

Product 1

HCID 24905198HCID 24905198, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-(4-amino-3-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA20d) (30 mg, 0.10 mmol) was dissolved in DMF (0.400 ml). K2CO3 (55 mg, 0.4 mmol) was added and reaction was stirred at 70° C. 3-bromo-1-propanol (0.050 ml, 0.6 mmol) was added and reaction was stirred overnight. Solid K2CO3 was removed by filtration. Solvent was partially removed in vacuo. Sodium citrate (50 ml) was added and reaction was extracted with saturated NaCl and CH2Cl2. Organic phases concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA99 (8.4 mg, 24% yield). ESI-MS (M+H)+ m/z calcd 357.2, found 357.1.

Workup

  1. customreaction
  2. customreaction
  3. stirringwas stirred overnight
  4. customSolid K2CO3 was removed by filtration
  5. customSolvent was partially removed in vacuo
  6. additionSodium citrate (50 ml) was added
  7. customreaction
  8. extractionwas extracted with saturated NaCl and CH2Cl2
  9. concentrationOrganic phases concentrated in vacuo
  10. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)

Sources & evidence

ORD record
ord-f06104a383ac4514a29dbdab94cb5e75
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

Loading…