Triethylamine → 5-(8-{4-[(Dimethylamino)acetyl]piperazin-1-yl}-9-isobutyl-6-morpholin-4-yl-9H-purin-2-yl)pyrimidin-2-amine

HRID 421361Notes

Reaction equation

HRID 421361 reaction equation
O.ON1C2C=CC=CC=2N=N1.Cl.CN(CCCN=C=NCC)C.C(N(CC)CC)C.[CH2:31]([N:35]1[C:43]([N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)=[N:42][C:41]2[C:36]1=[N:37][C:38]([C:56]1[CH:57]=[N:58][C:59]([NH2:62])=[N:60][CH:61]=1)=[N:39][C:40]=2[N:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1)[CH:32]([CH3:34])[CH3:33].Cl.[CH3:64][N:65]([CH3:70])[CH2:66][C:67](O)=[O:68]>ClCCl.CO.CN(C)C=O>[CH3:64][N:65]([CH2:66][C:67]([N:47]1[CH2:48][CH2:49][N:44]([C:43]2[N:35]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:36]3[C:41]([N:42]=2)=[C:40]([N:50]2[CH2:55][CH2:54][O:53][CH2:52][CH2:51]2)[N:39]=[C:38]([C:56]2[CH:61]=[N:60][C:59]([NH2:62])=[N:58][CH:57]=2)[N:37]=3)[CH2:45][CH2:46]1)=[O:68])[CH3:70]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 75605N,N-Dimethylglycine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 593335015-(9-Isobutyl-6-morpholino-8-(piperazin-1-yl)-9H-purin-2-yl)pyrimidin-2-amine

Product 1

HCID 453780175-(8-{4-[(Dimethylamino)acetyl]piperazin-1-yl}-9-isobutyl-6-morpholin-4-yl-9H-purin-2-yl)pyrimidin-2-amineYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

1-Hydroxybenzotriazole monohydrate (48.9 mg, 0.32 mmol), 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (91.8 mg, 0.48 mmol), and triethylamine (164.6 μl, 1.18 mmol) were added to an N,N-dimethylformamide suspension (2.0 ml) of 5-[9-(isobutyl)-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl]pyrimidin-2-amine (140.0 mg, 0.32 mmol) and N,N-dimethylglycine hydrochloride (53.5 mg, 0.38 mmol) at room temperature. The resulting mixture was stirred for 21 hour and then the reaction mixture was poured into dichloromethane-methanol (10:1), washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by preparative thin layer silica gel chromatography (dichloromethane:methanol=5:1) to give the title compound (103.9 mg, 62%) as a pale yellow solid.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by preparative thin layer silica gel chromatography (dichloromethane:methanol=5:1)

Sources & evidence

ORD record
ord-efb25123bace4c74bbb7a1714f09690a
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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