1,1'-Carbonyldiimidazole → HCID 53633805, compound

HRID 974775Notes

Reaction equation

HRID 974775 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16].[N:27]1([C:32]2[N:37]=[C:36]([N:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)[CH:35]=[C:34]([N:44]3[CH2:48][CH2:47][CH2:46][CH2:45]3)[N:33]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1.P([O-])(O)(O)=O.[Na+]>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH:9]1[CH2:10][O:11][C:15]([N:41]1[CH2:42][CH2:43][N:38]([C:36]2[CH:35]=[C:34]([N:44]3[CH2:45][CH2:46][CH2:47][CH2:48]3)[N:33]=[C:32]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[N:37]=2)[CH2:39][CH2:40]1)=[O:16])=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 643448(S)-(-)-N-Boc-prolinolHCID 145852434-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidineHCID 23672064Monosodium phosphate

Product 1

HCID 53633805HCID 53633805, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3 g of BOC-(L)-prolinol in 100 ml of anhydrous THF, cooled at 0° C. with water/ice, under stirring and inert gas atmosphere, is added with 2.9 g of carbonyldiimidazole in portions, then the reaction mixture is warmed to room temperature and stirring is continued for 3 hours. Said solution is added with 4.5 g of N-[2,6-bis(pyrrolidin-1-yl)pyrimidin-4-yl]piperazine in portions and stirring is continued for 18 hours. The reaction mixture is added with 400 ml of an aqueous saturated solution of sodium dihydrogen phosphate and extracted with ethyl acetate (3×100 ml). The combined organic extracts are dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue (7.5 g) is purified by silica gel chromatography (eluent hexane/ethyl acetate 7:3), to obtain 5.5 g of (-)-N'-[(1-(tertbutoxycarbonyl) pyrrolidin-2-yl) methyloxycarbonyl]-N-[2,6-bis(pyrrolidin -1-yl)pyrimidin -4 -yl]piperazine, m.p. 147° C., [(α]D-32'(c=0.25 in EtOH).

Workup

  1. stirringstirring
  2. stirringstirring
  3. waitis continued for 18 hours
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. dry with materialThe combined organic extracts are dried over sodium sulfate
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe residue (7.5 g) is purified by silica gel chromatography (eluent hexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-88e3e0aed66c403d849bbae06b643840
Source dataset
uspto-grants-1997_03
Patent number
US05607930

Reaction notes

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