Diisopropylethylamine → HCID 178455231, compound

HRID 1678013Notes

Reaction equation

HRID 1678013 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[NH:6]2.[Si:18]([O:25][C@@H:26]1[C@H:30]([CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:29][C@@H:28]([NH2:40])[CH2:27]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(N(CC)C(C)C)(C)C>C(O)C>[Si:18]([O:25][C@@H:26]1[C@H:30]([CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:34])[CH3:35])[CH2:29][C@@H:28]([NH:40][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[NH:6]3)[CH2:27]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59671204(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanamineHCID 178478055HCID 178478055, compound

Product 1

HCID 178455231HCID 178455231, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-chloro-8-(3-chlorophenyl)-9H-purine (155 mg, 0.58 mmol), (1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanamine (200 mg, 0.56 mmol) (Example 128, steps a-c), and N,N-diisopropylethylamine (0.20 mL, 1.17 mmol) in ethanol (2.00 mL) was microwaved at 160° C. for 30 minutes. The reaction mixture was concentrated under vacuum, and the residue was purified by flash chromatography (0 to 5% Methanol/DCM) to afford the title compound (275 mg, 76%) as a light yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified by flash chromatography (0 to 5% Methanol/DCM)

Sources & evidence

ORD record
ord-6133301149c645c8bf9f0aca884adb2e
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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