Glycolic Acid → 2-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-2-oxoethanol

HRID 421378

Reaction equation

HRID 421378 reaction equation
[OH:1][CH2:2][C:3]([OH:5])=O.O.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.FC(F)(F)C(O)=O.[N:36]1([C:42]2[N:50]=[C:49]([C:51]3[CH:52]=[N:53][C:54]([NH2:57])=[N:55][CH:56]=3)[N:48]=[C:47]3[C:43]=2[N:44]=[C:45]([N:63]2[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]2)[N:46]3[CH2:58][C:59]([F:62])([F:61])[F:60])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C(N(CC)CC)C.CN(C)C=O>[NH2:57][C:54]1[N:55]=[CH:56][C:51]([C:49]2[N:48]=[C:47]3[C:43]([N:44]=[C:45]([N:63]4[CH2:68][CH2:67][N:66]([C:3](=[O:5])[CH2:2][OH:1])[CH2:65][CH2:64]4)[N:46]3[CH2:58][C:59]([F:60])([F:62])[F:61])=[C:42]([N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)[N:50]=2)=[CH:52][N:53]=1

Participants

7

Reactant 4

HCID 757Glycolic 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 593335412-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-2-oxoethanolYield 78.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2-Hydroxyacetic acid (15 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 4 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 (70 mg) 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-62fbc99935d943b1a64d64bb7278260c
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Linked notes

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