Diisopropylethylamine → 6-[4-(2-Morpholin-4-ylethyl)piperazin-1-yl]pyrimidin-4-amine

HRID 1241368

Reaction equation

HRID 1241368 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.C(N(C(C)C)CC)(C)C.[N:18]1([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C(O)CCC>[N:26]1([CH2:25][CH2:24][N:18]2[CH2:19][CH2:20][N:21]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=3)[CH2:22][CH2:23]2)[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2380124-Amino-6-chloropyrimidineHCID 27346404-(2-Piperazin-1-yl-ethyl)-morpholine

Product 1

HCID 219346006-[4-(2-Morpholin-4-ylethyl)piperazin-1-yl]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
125 °C

Procedure

6-chloropyrimidin-4-amine 7-2 (3.09 g, 23.9 mmol) and diisopropylethylamine (3.08 g, 23.9 mmol) were suspended in n-butanol and then 4-(2-piperazin-1-ylethyl)morpholine 7-3 (4.75 g, 23.9 mmol) was added. The reaction was stirred at 125° C. for 18 hours and then the product was filtered off, washed with n-butanol and ethyl ether and then air dried. Hi-Res MS: calc: 293.2084 found: 293.2078. 1H-NMR (DMSO): 7.94 ppm (s, 1H); 6.18 ppm (s, 2H); 5.57 ppm (s, 1H); 3.56 ppm (m, 6H); 3.39 ppm (m, 8H); 2.47 ppm (m, 6H).

Workup

  1. filtrationthe product was filtered off
  2. washwashed with n-butanol and ethyl ether
  3. customair dried

Sources & evidence

ORD record
ord-0481e34e5d6b4bfa9e73dc34b97ef510
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Linked notes

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