Hexane → HCID 86584210, compound

HRID 2181599Notes

Reaction equation

HRID 2181599 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[CH3:12][Si:13]([CH2:16][CH2:17][O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:20])([CH3:15])[CH3:14].CCOC(C)=O.CCCCCC>C(Cl)Cl.CO>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([CH:22]2[CH2:23][NH:24][CH2:25][CH2:26][N:21]2[C:19]([O:18][CH2:17][CH2:16][Si:13]([CH3:15])([CH3:14])[CH3:12])=[O:20])[N:3]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 53244122,6-DichloropurineHCID 22481450HCID 22481450, compound

Product 1

HCID 86584210HCID 86584210, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To 2,6-dichloropurine (8.86 g, 57.73 mmol) dissolved in a mixture of CH2Cl2 (200 mL), MeOH (50 mL) and DPEA (7.71 mL, 63.50 mmol) was added N1-(trimethylsilylethoxycarbonyl) piperazine (13.30 g, 57.73 mmol) as a solid. The reaction progress was monitored by thin layer chromatography MeOH:EtOAc:hexane (1/49/50, v/v/v) which showed disappearance of starting material and formation of a new product spot after 15 hours. The solvent was removed in vacuo and the residue left behind was partitioned between water (100 mL) and CH2Cl2 (100 mL). The water layer was separated and extracted twice with CH2Cl2 (50 mL). The CH2Cl2 fractions were combined and washed with brine (100 mL), dried (MgSO4), filtered and evaporated. The residue was purified by silica gel flash column chromatography using MeOH:EtOAc:CH2Cl2 (1/49/50, v/v/v) as the eluent. The appropriate fractions were pooled and evaporated to give 15.70 g (71%) of the title compound. 1H NMR (CDCl3): δ 0.02 (s, 9H), 1.04 (t, 2H), 3.69 (t, 4H), 4.25 (t, 2H), 4.40 (bs, 4AH), 7.99 (s, 1H), 13.5 (bs, NH).

Workup

  1. customafter 15 hours
  2. customThe solvent was removed in vacuo
  3. waitthe residue left
  4. custombehind was partitioned between water (100 mL) and CH2Cl2 (100 mL)
  5. customThe water layer was separated
  6. extractionextracted twice with CH2Cl2 (50 mL)
  7. washwashed with brine (100 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by silica gel flash column chromatography
  12. customevaporated

Sources & evidence

ORD record
ord-8ffce81c47414aa7be388d264fcba58a
Source dataset
uspto-grants-2005_05
Patent number
US06893815B1

Reaction notes

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