Trifluoroacetic acid → HCID 86667773, compound

HRID 629946Notes

Reaction equation

HRID 629946 reaction equation
CC1C=C(C)C=C(C)C=1S(O[C:14]1[C:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][C:33]([P:36]([O:41][CH2:42][CH3:43])([O:38][CH2:39][CH3:40])=[O:37])([F:35])[F:34])=[CH:23][C:22]=2[O:44][CH3:45])=[C:18]([CH3:46])[N:17]=[C:16]([NH2:47])[N:15]=1)(=O)=O.C(O)(C(F)(F)F)=O.[CH2:55]([NH2:60])[CH2:56][CH2:57][CH2:58][CH3:59]>CCOC(C)=O>[NH2:47][C:16]1[N:17]=[C:18]([CH3:46])[C:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][C:33]([P:36](=[O:37])([O:38][CH2:39][CH3:40])[O:41][CH2:42][CH3:43])([F:35])[F:34])=[CH:23][C:22]=2[O:44][CH3:45])=[C:14]([NH:60][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[N:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8060PentylamineHCID 86667774HCID 86667774, compound

Product 1

HCID 86667773HCID 86667773, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-amino-5-(4-(2-(3-(diethoxyphosphoryl)-3,3-difluoropropoxy)ethoxy)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate (1 equiv.) in EtOAc (0.20 M) was added TFA (1.1 equiv.) and amylamine (3.3 equiv.). The reaction mixture was then heated to 100° C. for 18 h. At this point the reaction mixture was allowed to cool to room temperature and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH™ system using a gradient of 0-10% MeOH/DCM to provide the title compound (76%) as a solid.

Workup

  1. temperatureto cool to room temperature
  2. customthe volatiles were removed in vacuo
  3. customThe resulting residue was purified by a COMBIFLASH™ system

Sources & evidence

ORD record
ord-b67c0d4e37b04540bfa6271d0be31e17
Source dataset
uspto-grants-2016_04
Patent number
US09315530B2

Reaction notes

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