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1-Butanol → racemic N2-(1-(1H-indol-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 475245
Notes
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Reaction equation

HRID 475245 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:13][N:12]=[C:11]([CH:14]3[CH2:16][CH2:15]3)[CH:10]=2)[CH:5]=[CH:4][N:3]=1.C(O)(=O)CCCCC(O)=O.[NH:27]1[C:35]2[C:30](=[CH:31][C:32]([CH:36]([NH2:38])[CH3:37])=[CH:33][CH:34]=2)[CH:29]=[CH:28]1.CCN(C(C)C)C(C)C.CCCCO>CCOC(C)=O>[NH:27]1[C:35]2[C:30](=[CH:31][C:32]([CH:36]([NH:38][C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:10]=[C:11]([CH:14]5[CH2:16][CH2:15]5)[NH:12][N:13]=4)[CH:5]=[CH:4][N:3]=3)[CH3:37])=[CH:33][CH:34]=2)[CH:29]=[CH:28]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 529934411-(1h-Indol-5-yl)ethylamine adipateHCID 178478345HCID 178478345, compound

Product 1

HCID 78059718racemic N2-(1-(1H-indol-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamineYield 24.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A vessel was charged with 53 (665 mg, 2.82 mmol), 1-(1H-indol-5-yl)ethanamine adipic acid salt (1.45 g mg, 6.20 mmol, CASRN 1282097-87-3), DIPEA (7.4 mL) and n-BuOH (57 mL), sealed and heated at 120° C. for 12 d. The reaction mixture was cooled and diluted with EtOAc. The organic layer was washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude was purified by reverse-phase HPLC purification to afford 250.0 mg (24.7%) of racemic N2-(1-(1H-indol-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (180) as a white solid.

Workup

  1. customsealed
  2. temperatureThe reaction mixture was cooled
  3. washThe organic layer was washed sequentially with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by reverse-phase HPLC purification

Sources & evidence

ORD record
ord-2f2701dac57e41a2b20a2c072227f41c
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637537B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes