Diisopropylethylamine → N4-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-((5-methyl-1H-indol-4-yl)methyl)pyrimidine-2,4-diamine

HRID 475299Notes

Reaction equation

HRID 475299 reaction equation
[CH3:1][C:2]1[C:3]([CH2:11][NH2:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.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>>[CH:26]1([C:23]2[NH:24][N:25]=[C:21]([NH:20][C:18]3[CH:17]=[CH:16][N:15]=[C:14]([NH:12][CH2:11][C:3]4[C:2]([CH3:1])=[CH:10][CH:9]=[C:8]5[C:4]=4[CH:5]=[CH:6][NH:7]5)[N:19]=3)[CH:22]=2)[CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 76846757(5-methyl-1H-indol-4-yl)methanamineHCID 178478345HCID 178478345, compound

Product 1

HCID 86694757N4-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-((5-methyl-1H-indol-4-yl)methyl)pyrimidine-2,4-diamine

Conditions

Temperature
120 °C

Procedure

A mixture of 304 (53 mg, 0.331 mmol) 53 (94 mg, 0.397 mmol), and DIPEA (128 mg, 0.993 mmol) in WA (2 mL) under nitrogen atmosphere was heated in a sealed tube at 120° C. for 18 h. The crude was purified by preparative HPLC to afford 38 mg (32%) of I-122.

Workup

  1. customThe crude was purified by preparative HPLC
  2. customto afford 38 mg (32%) of I-122

Sources & evidence

ORD record
ord-b4b8e60fe6c346e6bd1b0cf705e7f0a7
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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