Diisopropylethylamine → N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-tosyl-1H-indol-6-yl)methyl)pyrimidine-2,4-diamine

HRID 475180

Reaction equation

HRID 475180 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.[S:17]([N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([CH2:36][NH2:37])[CH:34]=2)[CH:29]=[CH:28]1)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18].CCN(C(C)C)C(C)C>CCCCO>[CH:14]1([C:11]2[NH:12][N:13]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:37][CH2:36][C:33]4[CH:34]=[C:35]5[C:30]([CH:29]=[CH:28][N:27]5[S:17]([C:20]5[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=5)(=[O:19])=[O:18])=[CH:31][CH:32]=4)[N:7]=3)[CH:10]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 71272360(1-tosyl-1H-indol-6-yl)methanamineHCID 178478345HCID 178478345, compound

Product 1

HCID 86694718N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-tosyl-1H-indol-6-yl)methyl)pyrimidine-2,4-diamineYield 96.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A microwave vial was charged with 53 (80 mg, 0.34 mmol), 36 (80 mg, 0.27 mmol), DIPEA (0.2 mL) and n-BuOH (2.0 mL), sealed and irradiated in a microwave reactor at 180° C. for 80 min. The reaction mixture was concentrated and purified with a CombiFlash® to afford 130 mg (95%) of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-tosyl-1H-indol-6-yl)methyl)pyrimidine-2,4-diamine (38) as yellow solid; MS (ESI) m/z=500.1 [M+1]+.

Workup

  1. customsealed
  2. customirradiated in a microwave reactor at 180° C. for 80 min
  3. concentrationThe reaction mixture was concentrated
  4. custompurified with a CombiFlash®

Sources & evidence

ORD record
ord-4a9b58dc613a48b19e3819d5e555b259
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Linked notes

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