Benzyl Chloride → HCID 67317020, compound

HRID 1012981Notes

Reaction equation

[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:21]([CH3:23])([CH3:22])[NH:20][CH2:19][CH2:18][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:32](Cl)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C>[CH2:32]([O:16][C:15]1[C:14](=[O:17])[N:13]2[CH2:18][CH2:19][NH:20][C:21]([CH3:22])([CH3:23])[C:12]2=[N:11][C:10]=1[C:8]([NH:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:25][CH:24]=1)=[O:9])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred solution of N-(4-fluorobenzyl)-3-hydroxy-9,9-dimethyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrazino[1,2-a]pyrimidine-2-carboxamide (see Example 1) in DMF was added K2CO3 (2 eq.) followed by BnCl (1.1 eq.). The mixture was stirred at 65° C. overnight, after which time additional BnCl (0.3 eq.) was added and the mixture was left for a further 6 hours. The solvent was removed under reduced pressure and the brown oil was taken into EtOAc, washed with 1N HCl and brine, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography, eluting with 2% MeOH/DCM to afford the title product. 1H NMR (300 MHz, d6-DMSO) δ 8.88 (t, J=6.2 Hz, 1H), 7.30-7.44 (m, 7H), 7.06 (t, J=8.8 Hz, 2H), 5.05 (s, 2H), 4.41 (d, J=6.2 Hz, 2H), 3.80 (t, J=5.4 Hz, 2H), 3.09 (br. s, 2H), 1.44 (s, 6H); MS (ES) C24H25FN4O3 requires 436. Found: 437 (M+H+).

Workup

waitthe mixture was left for a further 6 hours
customThe solvent was removed under reduced pressure
washwashed with 1N HCl and brine
dry with materialdried (Na2SO4)
customevaporated under reduced pressure
customThe residue was purified by flash column chromatography
washeluting with 2% MeOH/DCM

Sources & evidence

ORD record: ord-95fb5abdf9a740f287652107e15c9106
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981879B2

Reaction notes

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