Potassium Carbonate → HCID 22865097, compound

HRID 1078287Notes

Reaction equation

HRID 1078287 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 mmoles) 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 a temperature of 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 layer is dried and evaporated. The residue is purified by chromatography on a silica gel column by using a 98:2 mixture of chloroform/methanol as eluent. After recrystallization from ether the title compound is obtained in a yield of 2.48 g (88.5%), m.p.:210°-220° C.

Workup

  1. customevaporated
  2. customAfter separation the chloroform layer
  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 as eluent
  7. customAfter recrystallization from ether the title compound
  8. customis obtained in a yield of 2.48 g (88.5%), m.p.:210°-220° C.

Sources & evidence

ORD record
ord-86fde51454204551a8081b514d60408d
Source dataset
uspto-grants-1996_08
Patent number
US05547949

Reaction notes

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