1,4-Dibromobutane → HCID 178491842, compound

HRID 1435342Notes

Reaction equation

HRID 1435342 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]2)[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:35][CH2:36][CH2:37][CH2:38]Br>C(O)C>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([N:27]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH2:23][CH2:22]2)[N:3]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 10340Sodium CarbonateHCID 178491845HCID 178491845, compound

Product 1

HCID 178491842HCID 178491842, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of trans-[4-amino-2-(4-amino-cyclohexylamino)-pyrimidin-5-yl]-(2,3-difluoro-6-methoxy-phenyl)-methanone (64 mg, 0.16 mmol, Example 120) and sodium carbonate (0.49 mmol, 52 mg) in ethanol (3 mL), 1,4-dibromobutane (22 uL, 0.16 mmol, Aldrich) was added and the mixture was stirred at reflux for 3 days. The solvent was removed under reduced pressure and the residue was purified by reversed phase HPLC to give a white solid. 30 mg, 43%. MS (ES) MH+=432.

Workup

  1. temperatureat reflux for 3 days
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by reversed phase HPLC
  4. customto give a white solid

Sources & evidence

ORD record
ord-459ba63a07c342389b317a11cfb237f7
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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