4-(Methylsulfonyl)benzyl Bromide → HCID 86670113, compound

HRID 1631726Notes

Reaction equation

[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:27][S:28]([C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1)(=[O:30])=[O:29]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:35][C:34]3[CH:33]=[CH:32][C:31]([S:28]([CH3:27])(=[O:30])=[O:29])=[CH:38][CH:37]=3)[C:7](=[O:12])[CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x1, 1.5 g, 6.23 mmol) was dissolved in DMF (25 mL) to give an orange solution. The mixture was cooled to 0° C. and lithium bis(trimethylsilyl)amide (1.04 g, 6.23 mmol), followed by 4-methylsulfonylbenzyl bromide (1.71 g, 6.86 mmol), were added. The reaction mixture was stirred at 0° C. for 1 hour and was subsequently diluted with ethyl acetate and washed with brine (100 mL) to give a suspension. An orange precipitate was collected on a fitted glass funnel and was washed with water (3×20 mL) and dried over night in a stream of nitrogen. The crude solid was triturated with hot ethyl acetate (2×) to give the title compound which was used without further purification (1.78 g, 69.8%). ESI-MS m/z [M+H]+ calc'd for C17H17ClN4O4S, 409.07. found 409.3.

Workup

customto give an orange solution
additionwere added
washwashed with brine (100 mL)
customto give a suspension
customAn orange precipitate was collected on a fitted glass funnel
washwas washed with water (3×20 mL)
customdried over night in a stream of nitrogen
customThe crude solid was triturated with hot ethyl acetate (2×)

Sources & evidence

ORD record: ord-1a368e9ae88a4b3c87ed4877fa670463
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791107B2

Reaction notes

Loading…