4-(4-chlorophenoxy)Benzeneethanamine → HCID 178494129, compound

HRID 474878Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

5-(2-Methoxy-pyrimidin-5-ylmethyl)-2-methylsulfanyl-1H-pyrimidin-4-one (30 mg, 0.114 mmol, 1 eq) and 2-[4-(4-Chloro-phenoxy)-phenyl]-ethylamine (42.6 mg, 0.171 mmol, 1.5 eq) were dissolved in dry ethanol (300 μl) and stirred at 130° C. for overnight. Reaction mixture was evaporated and crude residue (72 mg) was sent to HPLC/MS Purification. After HPLC/MS purification combined fractions of desired product were collected and put on lyophilisation to obtain 2-{2-[4-(4-Chloro-phenoxy)-phenyl]-ethylamino}-5-(2-methoxy-pyrimidin-5-ylmethyl)-1H-pyrimidin-4-one (0.020 mmol; yield: 17.5%, HPLC-MS/UV: [M+H]+=464.93; rt: 10.93 min; purity: 95%). 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.77 (t, J=7.02 Hz, 2H), 3.39-3.52 (m, 4H), 3.84 (s, 3H), 6.49 (br.s., 1H), 6.88-7.03 (m, 4H), 7.24 (d, J=7.72 Hz, 2H), 7.40 (d, J=7.02, 2H), 7.61 (s, 1H), 8.44 (s, 2H), 10.92 (br.s., 1H)

Workup

customReaction mixture
customwas evaporated
customcrude residue (72 mg) was sent to HPLC/MS Purification
customAfter HPLC/MS purification
customwere collected

Sources & evidence

ORD record: ord-9a1dd6f0f6ad452d90635a3da2e7f150
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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