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Diisopropylethylamine → N-[(1S)-2,3-dihydro-1H-inden-1-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1678010
Notes
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Reaction equation

HRID 1678010 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:5]([NH:11][C@@H:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[N:6][CH:7]=[N:8][C:9]=1Cl.C(N(CC)C(C)C)(C)C>O1CCOCC1>[C@@H:12]1([NH:11][C:5]2[C:4]3[CH2:3][CH2:2][NH:1][C:9]=3[N:8]=[CH:7][N:6]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 596712355-(2-aminoethyl)-6-chloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]pyrimidin-4-amine

Product 1

HCID 59671196N-[(1S)-2,3-dihydro-1H-inden-1-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-amineYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

5-(2-aminoethyl)-6-chloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]pyrimidin-4-amine (1.00 g, 3.46 mmol) and N,N-diisopropylethylamine (1.21 mL, 6.92 mmol) were dissolved in 1,4-dioxane (19 mL) and the solution was heated in a pressure tube at 160° C. for 48 hours. At that time, LCMS indicated complete conversion. Solvent was removed in vacuo and the residue was purified using chromatography on silica gel using gradient 0 to 20% MeOH in methylene chloride to afford the title compound (0.81 g, 93%). LC/MS: Rt=1.55 min, ES+ 253 (AA standard).

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-cf050f55984b428a9ca2cf008a4b7796
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08008307B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes