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

HRID 415398
Notes
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Reaction equation

HRID 415398 reaction equation
Cl.[F:2][C:3]1[CH:4]=[N:5][C:6]([C@@H:9]([NH2:11])[CH3:10])=[N:7][CH:8]=1.Cl[C:13]1[N:18]=[C:17]([NH:19][C:20]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[NH:22][N:21]=2)[C:16]([F:28])=[CH:15][N:14]=1.CCN(C(C)C)C(C)C>CCCCO>[CH:25]1([C:23]2[NH:22][N:21]=[C:20]([NH:19][C:17]3[C:16]([F:28])=[CH:15][N:14]=[C:13]([NH:11][C@H:9]([C:6]4[N:7]=[CH:8][C:3]([F:2])=[CH:4][N:5]=4)[CH3:10])[N:18]=3)[CH:24]=2)[CH2:27][CH2:26]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581693062-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)-5-fluoropyrimidin-4-amineHCID 66624037(S)-1-(5-Fluoropyrimidin-2-yl)ethanamine hydrochloride

Product 1

HCID 16659681N4-(5-Cyclopropyl-1H-pyrazol-3-yl)-5-fluoro-N2-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]pyrimidine-2,4-diamineYield 242.5%

Reagents, catalysts & solvents 1

HCID 263
1-Butanol
Solvent

Conditions

Temperature
180 °C

Procedure

A mixture of (S)-1-(5-fluoropyrimidin-2-yl)ethanamine hydrochloride (Method 7, 93 mg), 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-fluoropyrimidin-4-amine (Method 16, 127 mg) and DIPEA (0.22 ml) in n-BuOH (2.5 ml) was charged into a microwave reaction vessel. The vessel was sealed and heated in microwave reactor at 180° C. for 6 hours. The solvent was removed under reduced pressure and the residue was purified by Gilson (10-50% MeCN/H2O, 15 minutes) to give the titled compound as solid (435 mg). NMR 11.28 (s, 1H), 8.92 (s, 3H), 8.24 (s, 1H), 6.04 (s, 1H), 4.92-5.54 (m, 1H), 1.82-1.98 (m, 1H), 1.56 (d, 3H), 0.94-1.06 (m, 2H), 0.64-0.80 (m, 2H). m/z 395.

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 Gilson (10-50% MeCN/H2O, 15 minutes)

Sources & evidence

ORD record
ord-fa2d970ea7b443f28b8b00adaca93b95
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