Diisopropylethylamine → N2-((1H-Indol-4-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methylpyrimidine-2,4-diamine

HRID 475292Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[C:5]([CH2:10][NH:11][CH3:12])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[C:14]1[N:19]=[C:18]([NH:20][C:21]2[NH:25][N:24]=[C:23]([CH:26]3[CH2:28][CH2:27]3)[CH:22]=2)[CH:17]=[CH:16][N:15]=1.CCN(C(C)C)C(C)C>CC(O)C>[NH:1]1[C:9]2[C:4](=[C:5]([CH2:10][N:11]([CH3:12])[C:14]3[N:19]=[C:18]([NH:20][C:21]4[CH:22]=[C:23]([CH:26]5[CH2:28][CH2:27]5)[NH:24][N:25]=4)[CH:17]=[CH:16][N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

A tube was charged with 116 (280 mg, 1.75 mmol), 53 (412 mg, 1.75 mmol), DIPEA (678 mg, 5.25 mmol) and IPA (5 mL), sealed and heated at 120° C. for 14 h. The mixture was concentrated in vacuo and the residue was purified by preparative HPLC to afford 260 mg (41.4%) of I-40.

Workup

customsealed
concentrationThe mixture was concentrated in vacuo
customthe residue was purified by preparative HPLC
customto afford 260 mg (41.4%) of I-40

Sources & evidence

ORD record: ord-7b0d12c3aaff4c66972a37c7c2206638
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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