L-Lactic Acid → (2S)-1-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-1-oxopropan-2-ol

HRID 1876568Notes

Reaction equation

HRID 1876568 reaction equation
[C:1]([OH:6])(=O)[C@H:2]([CH3:4])[OH:3].O.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.FC(F)(F)C(O)=O.[N:37]1([C:43]2[N:51]=[C:50]([C:52]3[CH:53]=[N:54][C:55]([NH2:58])=[N:56][CH:57]=3)[N:49]=[C:48]3[C:44]=2[N:45]=[C:46]([N:64]2[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]2)[N:47]3[CH2:59][C:60]([F:63])([F:62])[F:61])[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>C(N(CC)CC)C.CN(C)C=O>[NH2:58][C:55]1[N:56]=[CH:57][C:52]([C:50]2[N:49]=[C:48]3[C:44]([N:45]=[C:46]([N:64]4[CH2:69][CH2:68][N:67]([C:1](=[O:6])[C@@H:2]([OH:3])[CH3:4])[CH2:66][CH2:65]4)[N:47]3[CH2:59][C:60]([F:61])([F:63])[F:62])=[C:43]([N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)[N:51]=2)=[CH:53][N:54]=1

Participants

7

Reactant 4

HCID 107689L-Lactic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866419965-[6-Morpholin-4-yl-8-piperazin-1-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine trifluoroacetateHCID 178526939HCID 178526939, compound

Product 1

HCID 59333520(2S)-1-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-1-oxopropan-2-ol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

L-Lactic acid (17 mg, 0.19 mmol), hydroxybenzotriazole hydrate (37 mg, 0.19 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (37 mg, 0.19 mmol), dimethylformamide (3 ml), and triethylamine (100 μl) were added to 5-[6-morpholin-4-yl-8-piperazin-1-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine trifluoroacetate (120 mg, 0.17 mmol) and the resulting mixture was stirred for 5 hours. The reaction mixture was partitioned with ethyl acetate and water, the organic layer was washed with saturated aqueous sodium bicarbonate solution and dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=19:1) to give the title compound as a colorless solid.

Workup

  1. customThe reaction mixture was partitioned with ethyl acetate and water
  2. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-13d1da6b79db4ee9b8d3bbb15e9147a7
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

Loading…