Diisopropylethylamine → HCID 67164124, compound

HRID 552691Notes

Reaction equation

HRID 552691 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@H:11]3[C@@H:15]4[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]4[C@@H:13]([CH2:21][OH:22])[O:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C(N(C(C)C)CC)(C)C.[NH2:32][C@@H:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][CH2:34]1>C(O)CCC>[C@@H:33]1([NH:32][C:2]2[C:3]3[CH:10]=[CH:9][N:8]([C@H:11]4[C@@H:15]5[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]5[C@@H:13]([CH2:21][OH:22])[O:12]4)[C:4]=3[N:5]=[CH:6][N:7]=2)[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 70000841-Aminoindane, (S)-HCID 86654222HCID 86654222, compound

Product 1

HCID 67164124HCID 67164124, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of [(3aR,4R,6R,6aR)-6-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-methanol (574 mg, 1.76 mmol), diisopropylethylamine (1.2 mL, 7.04 mmol) and (S)-(+)-1-aminoindane (680 μL, 5.27 mmol) in n-butanol 3.3 mL) was divided into two portions and each portion was microwave irradiated at 190° C. for 900 s. The solvent was removed in vacuo and the combined crude portions were purified by silica gel chromatography (0 to 5% MeOH/CH2Cl2) to afford 460 mg (62% over two steps) of the title compound.

Workup

  1. customeach portion was microwave irradiated at 190° C. for 900 s
  2. customThe solvent was removed in vacuo
  3. customwere purified by silica gel chromatography (0 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8ef4fa5d3cac4cb494997fc6f43ca2ed
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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