Formaldehyde → HCID 178518126, compound

HRID 474891Notes

Reaction equation

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

Participants

Reactant 3

HCID 712Formaldehyde

HCID 31268Pyrrolidine

HCID 178516535HCID 178516535, compound

Product 1

HCID 178518126HCID 178518126, compoundYield 79.5%

Procedure

2-{2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-1H-pyrimidin-4-one (0.122 mmol, 1 eq), paraformaldehyde (3.66 mg, 0.112 mmol, 1 eq) and pyrrolidine (10 μl, 0.112 mmol, 1 eq) were refluxed for 90 mins. Solvent was evaporated in vacuo to give 2-{2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamino}-5-pyrrolidin-1-ylmethyl-1H-pyrimidin-4-one (0.089 mmol, yield: 73%, UPLC-MS/UV:[M+H]+=493.39; rt: 0.98 min; purity: 85%). 1H NMR (300 MHz; CDCl3) δ/ppm 1.88-1.91 (m, 4H), 2.68-2.76 (m, 4H), 2.90 (t, J=7.51, 2H), 3.60 (s, 2H), 3.61-3.68 (m, 2H), 6.89-6.96 (m, 2H), 7.02 (dd, J=8.93 J=3.12, 1H), 7.21-7.23 (m, 1H), 7.30 (d, J=2.97, 1H), 7.40 (d, J=9.07, 1H), 7.74 (s, 1H)

Workup

customSolvent was evaporated in vacuo

Sources & evidence

ORD record: ord-941a84ba10b34d17a971e12f95c0bebc
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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