Diisopropylethylamine → N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 552723Notes

Reaction equation

HRID 552723 reaction equation
Cl[C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.CCN(C(C)C)C(C)C.[NH2:20][C@@H:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1>C(O)CCC>[C@@H:21]1([NH:20][C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 70000841-Aminoindane, (S)-HCID 178418725HCID 178418725, compound

Product 1

HCID 58944690N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 80%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (2.10 g, 13.6 mmol), DIPEA (3.57 mL, 20.5 mmol) and (S)-(+)-1-aminoindan (1.93 mL, 15.0 mmol) in 1-butanol (60.0 mL) and was heated to reflux for 60 hours, cooled down to room temperature and concentrated. The residue was purified by flash chromatography (0 to 100% EtOAc/DCM) to afford the title compound (2.72 g, 80%).

Workup

  1. temperatureto reflux for 60 hours
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (0 to 100% EtOAc/DCM)

Sources & evidence

ORD record
ord-024d7235da7d45eab9409ce6cf2ac4c2
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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