Diisopropylethylamine → HCID 136102579, compound

HRID 1993437Notes

Reaction equation

[N:1]1([C:7]2[N:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:14][C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[CH2:18]N1CCNCC1.C(N(C(C)C)CC)(C)C>CC(O)CC>[F:14][C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[CH2:18][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[N:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-chloro-3H-pyrimidin-4-one (Intermediate 4; 100 mg, 0.77 mmol), 1-(3-fluorobenz-yl)piperazine (Aldrich; 194 mg, 1.0 mmol), and diisopropylethylamine (200 μL, 1.1 mmol) in 2-butanol (5 mL) was heated in a sealed scintillation vial on a hot plate at about 80° C. for 8 hours and then allowed to cool and stand at room temperature overnight. The mixture was filtered. The solid was washed with 2-butanol and air-dried to give 6-[4-(3-fluoro-benzyl)-piperazin-1-yl]-3H-pyrimidin-4-one (145 mg, 65%), as a white solid, mp 273-275° C. (dec.). 1H NMR (d6-DMSO) δ 2.36-2.39 (m, 4H), 3.44-3.47 (m, 4H), 5.23 (s, 1H), 7.04-7.16 (m, 3H), 7.32-7.40 (m, 1H), 7.86 (s, 1H), 11.60 (s, 1H). LRMS ES+M+H 289. HRMS Calcd. for C15H18FN4O (M+H), 289.1459. Found, 289.1459.

Workup

temperatureto cool
filtrationThe mixture was filtered
washThe solid was washed with 2-butanol
customair-dried

Sources & evidence

ORD record: ord-633a2684e4e94fb680744de061cccea4
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652013B2

Reaction notes

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