Potassium Carbonate → HCID 22865097, compound

HRID 1078971Notes

Reaction equation

HRID 1078971 reaction equation
[C:1]12([NH:11][C:12]3[N:17]=[C:16]([NH:18][C:19]45[CH2:28][CH:23]6[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]6)[CH2:20]4)[CH2:26]5)[CH:15]=[C:14]([N:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)[N:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].BrC1C=CC(S(O[CH2:52][C:53](=[O:75])[C@@H:54]2[C@:71]3([CH3:72])[C@H:57]([C@H:58]4[C:68](=[CH:69][CH2:70]3)[C@:66]3([CH3:67])[C:61](=[CH:62][C:63](=[O:73])[CH:64]=[CH:65]3)[CH2:60][CH2:59]4)[CH2:56][C@H:55]2[CH3:74])(=O)=O)=CC=1>C(#N)C>[C:1]12([NH:11][C:12]3[N:17]=[C:16]([NH:18][C:19]45[CH2:28][CH:23]6[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]6)[CH2:20]4)[CH2:26]5)[CH:15]=[C:14]([N:29]4[CH2:30][CH2:31][N:32]([CH2:52][C:53](=[O:75])[C@@H:54]5[C@:71]6([CH3:72])[C@H:57]([C@H:58]7[C:68](=[CH:69][CH2:70]6)[C@:66]6([CH3:67])[C:61](=[CH:62][C:63](=[O:73])[CH:64]=[CH:65]6)[CH2:60][CH2:59]7)[CH2:56][C@H:55]5[CH3:74])[CH2:33][CH2:34]4)[N:13]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19428497HCID 19428497, compoundHCID 57282319HCID 57282319, compound

Product 1

HCID 22865097HCID 22865097, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

After adding 1.88 g (4.07 moles) of 2,4-bis(1-adamantylamino)-6-(1-piperazinyl)pyrimidine and 0.56 g of potassium carbonate to a solution containing 2.00 g (3.57 mmoles) of 21-(4-bromobenzenesulfonyloxy)-16α-methylpregna-1,4,9(11)-triene-3,20-dione in 100 ml of acetonitrile, the reaction mixture is stirred at 65° C. for 5 hours, then evaporated. The residue is distributed between 40 ml of chloroform and 10 ml of water. After separation the chloroform solution is dried, evaporated and the residue is purified by chromatography on a silica gel column. A 98:2 mixture of chloroform/methanol is used for elution and the product obtained is recrystallized from ether to give the title compound in a yield of 2.48 g (88.5%), m.p.: 210°-220° C.

Workup

  1. customevaporated
  2. customAfter separation the chloroform solution
  3. customis dried
  4. customevaporated
  5. customthe residue is purified by chromatography on a silica gel column
  6. additionA 98:2 mixture of chloroform/methanol
  7. washis used for elution
  8. customthe product obtained
  9. customis recrystallized from ether

Sources & evidence

ORD record
ord-1c0f7d3038114ef097e52c042c96f8c9
Source dataset
uspto-grants-1996_08
Patent number
US05550240

Reaction notes

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