Diisopropylethylamine → 1-(2-Chloro-6-morpholinopyrimidin-4-yl)piperidin-2-one

HRID 1043815Notes

Reaction equation

HRID 1043815 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl:44][C:45]1[N:50]=[C:49]([NH:51][CH2:52][CH2:53][CH2:54][CH2:55][C:56](O)=[O:57])[CH:48]=[C:47]([N:59]2[CH2:64][CH2:63][O:62][CH2:61][CH2:60]2)[N:46]=1>C(Cl)(Cl)Cl>[Cl:44][C:45]1[N:50]=[C:49]([N:51]2[CH2:52][CH2:53][CH2:54][CH2:55][C:56]2=[O:57])[CH:48]=[C:47]([N:59]2[CH2:64][CH2:63][O:62][CH2:61][CH2:60]2)[N:46]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866458885-(2-Chloro-6-morpholinopyrimidin-4-ylamino)pentanoic acid

Product 1

HCID 866458891-(2-Chloro-6-morpholinopyrimidin-4-yl)piperidin-2-oneYield 35%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of HATU (304 mg, 0.8 mmol), HOAT (82 mg, 0.6 mmol) and DIEA (0.209 mL, 1.2 mmol) in chloroform (20 mL) under argon, a solution of 5-(2-chloro-6-morpholinopyrimidin-4-ylamino)pentanoic acid (190 mg, 0.6 mmol) in chloroform (10 mL) was slowly added. The reaction solution was stirred at room temperature for 5 hours. After the reaction was complete, the solution was evaporated to dryness to give a white solid which was chromatographed on a silica gel column by eluting with 40% EtOAc/hexane to give 1-(2-chloro-6-morpholinopyrimidin-4-yl)piperidin-2-one as a white solid (62 mg, 35%). LC/MS (m/z): 297.0 (MH+), Rt 2.74 minutes.

Workup

  1. customthe solution was evaporated to dryness
  2. customto give a white solid which
  3. customwas chromatographed on a silica gel column
  4. washby eluting with 40% EtOAc/hexane

Sources & evidence

ORD record
ord-a50b16471a4940a5ab8e3499569fd620
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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