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Diisopropylethylamine → 5-Bromo-N2-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-N4-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 415396
Notes
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Reaction equation

HRID 415396 reaction equation
[Br:1][C:2]1[C:3]([NH:9][C:10]2[CH:14]=[C:13]([O:15][CH:16]([CH3:18])[CH3:17])[NH:12][N:11]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.Cl.[F:20][C:21]1[CH:22]=[N:23][C:24]([C@@H:27]([NH2:29])[CH3:28])=[N:25][CH:26]=1.CCN(C(C)C)C(C)C>CCCCO>[Br:1][C:2]1[C:3]([NH:9][C:10]2[CH:14]=[C:13]([O:15][CH:16]([CH3:18])[CH3:17])[NH:12][N:11]=2)=[N:4][C:5]([NH:29][C@H:27]([C:24]2[N:25]=[CH:26][C:21]([F:20])=[CH:22][N:23]=2)[CH3:28])=[N:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66624037(S)-1-(5-Fluoropyrimidin-2-yl)ethanamine hydrochlorideHCID 1784586132-chloro-5-bromo-N-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidin-4-amine

Product 1

HCID 1784586625-Bromo-N2-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-N4-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidine-2,4-diamineYield 60%

Reagents, catalysts & solvents 1

HCID 263
1-Butanol
Solvent

Conditions

Temperature
165 °C

Procedure

A mixture of 5-bromo-2-chloro-N-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidin-4-amine (Method 13, 150 mg, 0.45 mmol), (S)-1-(5-fluoropyrimidin-2-yl)ethanamine hydrochloride (Method 7, 88 mg, 0.5 mmol) and DIPEA (0.12 ml) in n-BuOH (2 ml) was charged into a microwave reaction vessel. The vessel was sealed and heated in microwave reactor at 165° C. for 4 hours. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel (20-60% EtOAc in hexanes) to give the titled compound as solid (118 mg, 60%). NMR: 11.98 (s, 1H), 9.36 (s, 1H), 8.82 (s, 2H), 8.10 (s, 1H), 7.96 (s, 1H), 5.56 (s, 1H), 5.13 (s, 1H), 4.66 (m, 1H), 1.48 (m, 3H), 1.26 (m, 6H); m/z 437.

Workup

  1. additionwas charged into a microwave reaction vessel
  2. customThe vessel was sealed
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (20-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-233cc4becb25400cbd1688d78ed5ca16
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08088784B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes