Succinic anhydride → HCID 10458073, compound

HRID 720632Notes

Reaction equation

HRID 720632 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11](=[O:24])[N:10]([CH2:25][CH2:26][CH2:27][CH3:28])[C:9]=3[N:8]=2)=[CH:4][CH:3]=1.[C:31]1(=O)[O:36][C:34](=[O:35])[CH2:33][CH2:32]1>CN(C)C=O>[CH2:17]([N:12]1[C:13](=[O:16])[C:14]2[NH:15][C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([N:1]4[C:34](=[O:35])[CH2:33][CH2:32][C:31]4=[O:36])=[CH:30][CH:29]=3)=[N:8][C:9]=2[N:10]([CH2:25][CH2:26][CH2:27][CH3:28])[C:11]1=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 21891802HCID 21891802, compound

Product 1

HCID 10458073HCID 10458073, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-(4-amino-benzyl)-1-benzyl-3-butyl-3,7-dihydro-purine-2,6-dione (60 mg) (prepared as described in example 64) in N,N-dimethylformamide (2 mL) was added succinic anhydride (Aldrich) (20 mg) and the mixture stirred at RT under argon for 48 h. The reaction mixture was concentrated in vacuo and acetyl chloride (Aldrich) (2 mL) added to the residue. After stirring at RT for an additional 70 h saturated aqueous sodium bicarbonate (5 mL) was added cautiously to the reaction mixture. The mixture was poured into water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Purified by crystallization from methanol/water to give the desired product as a pale yellow solid (36%). Mp=208–212° C. MS, m/z(M+)=485.2064.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and acetyl chloride (Aldrich) (2 mL)
  2. additionadded to the residue
  3. stirringAfter stirring at RT for an additional 70 h saturated aqueous sodium bicarbonate (5 mL)
  4. additionwas added cautiously to the reaction mixture
  5. additionThe mixture was poured into water
  6. extractionextracted with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated in vacuo
  10. customPurified by crystallization from methanol/water

Sources & evidence

ORD record
ord-008e8512599847d38adb3a6401dbb0a1
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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