Iodine → HCID 18362930, compound

HRID 322827Notes

Reaction equation

HRID 322827 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:11]=[C:5]2[N:4]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:3]1=[O:27].C([N-]C(C)C)(C)C.[Li+].[I:36]I.[Cl-].[NH4+]>O1CCCC1>[I:36][C:9]1[N:10]([CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)[CH:11]=[C:5]2[C:6]=1[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:27])[N:4]2[CH2:23][CH:24]([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 5282550HCID 5282550, compound

Product 1

HCID 18362930HCID 18362930, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

3-Methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo-[3,4-d]pyrimidine-2,4(3H,6H)-dione ((J. Med. Chem., 1995, 38, 2557; 500 mg) was dissolved in tetrahydrofuran (15 ml) and cooled to −78° C. A solution of lithium diisopropylamide (2 eq) in tetrahydrofuran (5 ml) was added dropwise with stirring at −78° C. Iodine (350 mg) was added and the reaction mixture was allowed to stir at −78° C. for 1 hour and was then allowed to warm to room temperature. The mixture was then poured into saturated ammonium chloride solution and extracted twice with ethyl acetate. The combined organic phases were washed with sodium thiosulphate solution, and with brine, before being dried and evaporated. The resultant foam was chromatographed using isohexane:diethyl ether (1:3) to give a foam which was recrystallised from diethyl ether/isohexane to give the subtitle compound as a pale yellow solid (350 mg).

Workup

  1. stirringto stir at −78° C. for 1 hour
  2. temperatureto warm to room temperature
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic phases were washed with sodium thiosulphate solution
  5. dry with materialwith brine, before being dried
  6. customevaporated
  7. customThe resultant foam was chromatographed
  8. customto give a foam which
  9. customwas recrystallised from diethyl ether/isohexane

Sources & evidence

ORD record
ord-cbec68d005354058bf4b362376da3ef3
Source dataset
uspto-grants-2001_04
Patent number
US06211368B1

Reaction notes

Loading…