1-Adamantanecarbonyl chloride → HCID 22402381, compound

HRID 486015Notes

Reaction equation

HRID 486015 reaction equation
[CH2:1]([N:4]1[C:11]([NH2:12])=[C:10]([NH2:13])[C:8](=[O:9])[N:7]([CH2:14][CH2:15][CH3:16])[C:5]1=[O:6])[CH2:2][CH3:3].[C:17]12([C:27](Cl)=[O:28])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2>N1C=CC=CC=1>[NH2:12][C:11]1[N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:6])[N:7]([CH2:14][CH2:15][CH3:16])[C:8](=[O:9])[C:10]=1[NH:13][C:27]([C:17]12[CH2:26][CH:21]3[CH2:20][CH:19]([CH2:25][CH:23]([CH2:22]3)[CH2:24]1)[CH2:18]2)=[O:28]

Participants

4

Reactant 2

HCID 989151-Adamantanecarbonyl chlorideHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 22402381HCID 22402381, compoundYield 113.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

At first, 10 g (44.3 mmol) of 1,3-dipropyl-5,6-diaminouracil was dissolved in 50 ml of pyridine, and 10.6 g (53.1 mmol) of adamantane-1-carbonylchloride was added by portions thereto at 0° C. After stirring for 30 minutes at 0° C., the mixture was concentrated under reduced pressure. A saturated aqueous sodium bicarbonate was added thereto. The residue was extracted with chloroform three times. The organic layers were combined, washed with a saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Then pyridine was removed from the residue by means of azeotropy with toluene to afford 19.5 g (yield: 100%) of 6-amino-5-(adamantane-1-carbonylamino)-1,3-dipropyluracil.

Workup

  1. customat 0° C
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionA saturated aqueous sodium bicarbonate was added
  4. extractionThe residue was extracted with chloroform three times
  5. washwashed with a saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThen pyridine was removed from the residue by means of azeotropy with toluene

Sources & evidence

ORD record
ord-7efc199e841a476485545fe9106cd0e2
Source dataset
uspto-grants-1994_03
Patent number
US05290782

Reaction notes

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