Dimethylamine → HCID 15840654, compound

HRID 342593Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:22](=[O:23])[C:21](Cl)=[CH:20][N:19]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:18]3=[O:33])[CH2:10][CH2:9]2)=[C:4]([O:34][CH2:35][C:36]([F:39])([F:38])[F:37])[CH:3]=1.[CH3:40][NH:41][CH3:42]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:22](=[O:23])[C:21]([N:41]([CH3:42])[CH3:40])=[CH:20][N:19]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:18]3=[O:33])[CH2:10][CH2:9]2)=[C:4]([O:34][CH2:35][C:36]([F:39])([F:38])[F:37])[CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 3-(3-{4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propyl)-5-chloro-1-[2-(trimethylsilyl)ethoxymethyl]-2,4(1H,3H)-pyrimidinedione (0.5 g, 0.84 mmol), prepared as in Example 25, aqueous dimethylamine (40%, 3 mL) and ethanol (3 mL) was heated in a sealed tube 3 hours at 130° C. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (95:5+3% ammonium hydroxide) to give 3-(3-{4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propyl)-5-dimethylamino-1-[2-(trimethylsilyl)ethoxymethyl]-2,4(1H,3H)-pyrimidinedione (0.26 g, 0.44 mmol).

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (95:5+3% ammonium hydroxide)

Sources & evidence

ORD record: ord-b29f8d0b36ff44e598189da0162395b2
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859014

Reaction notes

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