Butylamine → HCID 178448852, compound

HRID 920657Notes

Reaction equation

HRID 920657 reaction equation
[Br:1][C:2]1[C:10]2[CH:9]=[N:8][C:7](Cl)=[N:6][C:5]=2[NH:4][CH:3]=1.I[CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+].[CH2:34]([NH2:38])[CH2:35][CH2:36][CH3:37]>O.C1COCC1.CS(C)=O>[Br:1][C:2]1[C:10]2[CH:9]=[N:8][C:7]([NH:38][CH2:34][CH2:35][CH2:36][CH3:37])=[N:6][C:5]=2[N:4]([CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]2)[CH:3]=1

Participants

8

Reactant 4

HCID 8007ButylamineHCID 11430Potassium CarbonateHCID 457897805-Bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidineHCID 178453931HCID 178453931, compound

Product 1

HCID 178448852HCID 178448852, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

A 10 mL microwave tube was charged with 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.23 g, 1.0 mmol), tert-butyl trans-4-(iodomethyl)cyclohexylcarbamate (0.51 g, 1.5 mmol), K2CO3 (0.28 g, 2.0 mmol), DMSO (1.5 mL) and THF (3 mL). The mixture was heated at 150° C. for 100 min in microwave. After the reaction mixture was cooled to ambient temperature, n-butylamine (0.18 g, 2.5 mmol) was added. The mixture was heated at 150° C. for 90 min in microwave. After cooling to ambient temperature, the reaction was poured into water and extracted with EtOAc (3×). The combined organic layer was dried (Na2SO4) and concentrated. The crude mixture was purified by Isco to provide tert-butyl trans-4-((5-bromo-2-(butylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)cyclohexylcarbamate (0.35 g, 73%) as a white solid. MS m/z 480.2 [M+H]+.

Workup

  1. temperatureAfter the reaction mixture was cooled to ambient temperature
  2. temperatureThe mixture was heated at 150° C. for 90 min in microwave
  3. temperatureAfter cooling to ambient temperature
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude mixture was purified by Isco

Sources & evidence

ORD record
ord-f6fdce4fbdd64bd2a974796ce54e7ba7
Source dataset
uspto-grants-2016_03
Patent number
US09273056B2

Reaction notes

Loading…