Diisopropylethylamine → HCID 69433361, compound

HRID 914727Notes

Reaction equation

HRID 914727 reaction equation
Cl.[Cl:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][C@H:9]([NH2:12])[CH2:10][CH3:11].Cl[C:14]1[N:22]=[CH:21][N:20]=[C:19]2[C:15]=1[N:16]=[CH:17][N:18]2[C@H:23]1[C@H:30]2[C@H:26]([O:27][C:28]([CH3:32])([CH3:31])[O:29]2)[C@@H:25]([CH2:33][F:34])[CH2:24]1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][C@H:9]([NH:12][C:14]1[N:22]=[CH:21][N:20]=[C:19]2[C:15]=1[N:16]=[CH:17][N:18]2[C@H:23]1[C@H:30]2[C@H:26]([O:27][C:28]([CH3:31])([CH3:32])[O:29]2)[C@@H:25]([CH2:33][F:34])[CH2:24]1)[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9973677HCID 9973677, compoundHCID 69877158HCID 69877158, compound

Product 1

HCID 69433361HCID 69433361, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

(R)-1-(3-Chloro-thiophen-2-ylmethyl)-propylamine hydrochloride (1.36 g, 6 mmoles) and 6-chloro-9-((3aS,4R,6S,6aR)-6-fluoromethyl-2,2-dimethyl-tetrahydro -cyclopenta-1,3-dioxol-4-yl)-9H-purine (1.63 g, 5 mmoles) prepared as described above were combined in nBuOH (40 ml), iPr2NEt (3.5 ml, 20 mmoles) was then added and the resulting solution was stirred at reflux under an argon atmosphere. After 5 h, the reaction mixture was cooled down to room temperature, partitioned between water, brine and EtOAc, the aqueous layer was separated and extracted two times with EtOAc. The combined organic layers were washed with brine and dried over sodium sulfate. The filtrate is concentrated under reduced pressure to give a residue which was purified by flash chromatography on silica gel eluting with 2% MeOH in CH2Cl2 to yield [(R)-1-(3-chloro-thiophen-2-ylmethyl)-propyl]-[9-((3aS,4R,6S,6aR)-6-fluoromethyl-2,2-dimethyl -tetrahydro-cylopenta-1,3-dioxol-4-yl)-9H-purin-6-yl]-amine

Workup

  1. temperatureat reflux under an argon atmosphere
  2. custompartitioned between water, brine and EtOAc
  3. customthe aqueous layer was separated
  4. extractionextracted two times with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customto give a residue which
  9. customwas purified by flash chromatography on silica gel eluting with 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-223d1f3a8c774aab9483c8c4dc0c2403
Source dataset
uspto-grants-2007_09
Patent number
US07265111B2

Reaction notes

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