4-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidine → HCID 69223635, compound

HRID 326502Notes

Reaction equation

HRID 326502 reaction equation
[OH:1][C@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:24])[C@H:8]3[CH2:9][C@@H:10]([CH3:25])[C@@H:11]2[C:12](=[O:15])[CH2:13]I)[CH2:3]1.[N:26]1([C:31]2[N:36]=[C:35]([N:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)[CH:34]=[C:33]([N:43]3[CH2:47][CH2:46][CH2:45][CH2:44]3)[N:32]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C=O)C>[OH:1][C@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:24])[C@H:8]3[CH2:9][C@@H:10]([CH3:25])[C@@H:11]2[C:12](=[O:15])[CH2:13][N:40]2[CH2:41][CH2:42][N:37]([C:35]3[CH:34]=[C:33]([N:43]4[CH2:47][CH2:46][CH2:45][CH2:44]4)[N:32]=[C:31]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[N:36]=3)[CH2:38][CH2:39]2)[CH2:3]1

Participants

4

Reactant 2

HCID 145852434-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidineHCID 86745586HCID 86745586, compound

Product 1

HCID 69223635HCID 69223635, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3β-Hydroxy-21-iodo-16α-methylpregn-5-en-20-one (10 g) is added all at once to 4-[2,6-bis(1-pyrrolidinyl)-4-pyrimidinyl]piperazine (16 g) in DMF (400 ml) at 65° and then concentrated to 50 ml under reduced pressure. The concentrate is added to sodium dihydrogen phosphate (0.3M, 400 ml) and ethyl acetate (500 ml). The pH is adjusted to 4.5 with 0.3M phosphoric acid. The ethyl acetate layer is separated and extracted with sodium dihydrogen phosphate (0.3M, 2×200 ml). The ethyl acetate extract is then washed with phosphoric acid (0.3M, 400 ml). The acid extract is stirred and the ph is adjusted to 3.5 with sodium hydroxide (10%). The resulting precipitate is filtered, washed with water (200 ml) and dried to give the title compound.

Workup

  1. concentrationconcentrated to 50 ml under reduced pressure
  2. additionThe concentrate is added to sodium dihydrogen phosphate (0.3M, 400 ml) and ethyl acetate (500 ml)
  3. customThe ethyl acetate layer is separated
  4. extractionextracted with sodium dihydrogen phosphate (0.3M, 2×200 ml)
  5. extractionThe ethyl acetate extract
  6. washis then washed with phosphoric acid (0.3M, 400 ml)
  7. extractionThe acid extract
  8. filtrationThe resulting precipitate is filtered
  9. washwashed with water (200 ml)
  10. customdried

Sources & evidence

ORD record
ord-849fcf9df5714a9d90cad13d0883e44f
Source dataset
uspto-grants-1993_12
Patent number
US05268477

Reaction notes

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