Dichloromethane → HCID 59333599, compound

HRID 1876612Notes

Reaction equation

HRID 1876612 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].C(Cl)Cl.[CH2:18]1[C:20]2([CH2:25][N:24]([C:26]3[N:27]([CH2:48][C:49]([F:52])([F:51])[F:50])[C:28]4[C:33]([N:34]=3)=[C:32]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[N:31]=[C:30]([C:41]3[CH:42]=[N:43][C:44]([NH2:47])=[N:45][CH:46]=3)[N:29]=4)[CH2:23][CH2:22][NH:21]2)[CH2:19]1>C(Cl)Cl.CO>[C:8]([N:21]1[CH2:22][CH2:23][N:24]([C:26]2[N:27]([CH2:48][C:49]([F:52])([F:51])[F:50])[C:28]3[C:33]([N:34]=2)=[C:32]([N:35]2[CH2:36][CH2:37][O:38][CH2:39][CH2:40]2)[N:31]=[C:30]([C:41]2[CH:42]=[N:43][C:44]([NH2:47])=[N:45][CH:46]=2)[N:29]=3)[CH2:25][C:20]21[CH2:19][CH2:18]2)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59333566HCID 59333566, compound

Product 1

HCID 59333599HCID 59333599, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Triethylamine (56.8 μl, 0.41 mmol) and acetic anhydride (19.2 μl, 0.20 mmol) were added to a methylene chloride solution (3.0 ml) of 5-[8-(4,7-diazaspiro[2.5]oct-7-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine (83.3 mg, 0.17 mmol) at room temperature. The resulting mixture was stirred at room temperature for 2 hours and then the reaction mixture was poured into methylene chloride-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 (methylene chloride:methanol=10:1) to give the title compound (44.0 mg, 49%) as a light brown 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 (methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-1909dce9cd2f495f95de9506553c65ba
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

Loading…