HCID 131731318, compound → HCID 71727007, compound

HRID 2365886Notes

Reaction equation

HRID 2365886 reaction equation
[P:1]([O:19][CH2:20][C@H:21]([C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[C:44]([F:49])[CH:43]=1)[N:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][N:31]=[C:30]([NH:34][CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[N:29]=2)=[CH:24][C:23]1=[O:41])([O:11]CC1C=CC=CC=1)([O:3]CC1C=CC=CC=1)=[O:2]>[Pd].CO>[P:1]([OH:3])([OH:11])([O:19][CH2:20][C@H:21]([C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[C:44]([F:49])[CH:43]=1)[N:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][N:31]=[C:30]([NH:34][CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[N:29]=2)=[CH:24][C:23]1=[O:41])=[O:2]

Participants

4

Reactant 1

HCID 131731318HCID 131731318, compound

Product 1

HCID 71727007HCID 71727007, compoundYield 0.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5% Pd/C (0.15 g) was added to (S)-dibenzyl (2-(4-chloro-3-fluorophenyl)-2-(2-oxo-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-1(2H)-yl)ethyl) phosphate (978 mg) under nitrogen. MeOH (8 mL) was added, and the mixture was purged with a hydrogen balloon. The mixture was left under hydrogen overnight. The mixture was filtered through Celite®, and the solvent was removed to leave a solid. The solid was purified by HPLC to obtain (S)-2-(4-chloro-3-fluorophenyl)-2-(2-oxo-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-1(2H)-yl)ethyl dihydrogen phosphate (3.8 mg). MS=525.0.

Workup

  1. customthe mixture was purged with a hydrogen balloon
  2. filtrationThe mixture was filtered through Celite®
  3. customthe solvent was removed
  4. customto leave a solid
  5. customThe solid was purified by HPLC

Sources & evidence

ORD record
ord-d5e6c519457b4be6be556f277c6082bd
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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