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

HRID 222147Notes

Reaction equation

HRID 222147 reaction equation
Cl[C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.C(N(CC)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

4-Chloro-1H-pyrrolo[2,3-d]pyrimidine (2.10 g, 13.6 mmol) was dissolved in 1-butanol (60.0 mL) and N,N-diisopropylethylamine (3.57 mL, 20.5 mmol) was added followed by (S)-(+)-1-aminoindan (1.93 mL, 15.0 mmol). The mixture was heated to reflux for 60 h, cooled down to rt and the solvent was evaporated to dryness. The residue was purified via silica gel chromatography eluting with a gradient of 0 to 100% EtOAc in DCM to afford the title compound (2.72 g, 80%). LC/MS: Rt=1.42 min, ES+ 251 (AA standard).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 60 h
  3. customthe solvent was evaporated to dryness
  4. customThe residue was purified via silica gel chromatography
  5. washeluting with a gradient of 0 to 100% EtOAc in DCM

Sources & evidence

ORD record
ord-b34d0fdc6da043f3bf694db8c1f584dd
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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