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

HRID 475245Notes

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

Participants

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

customsealed
temperatureThe reaction mixture was cooled
washThe organic layer was washed sequentially with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
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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