1,3-Dibromo-5,5-dimethylhydantoin → HCID 59232194, compound

HRID 1099295Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:21]2[C:16]([C:17]([NH2:22])=[N:18][CH:19]=[N:20]2)=[CH:15][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:23]N1C(C)(C)C(=O)N(Br)C1=O>O1CCCC1>[Br:23][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3])[N:21]2[C:16]=1[C:17]([NH2:22])=[N:18][CH:19]=[N:20]2

Participants

Conditions

Temperature: -20 °C

Procedure

To a cooled (−20° C.) solution of 7-(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (5.60 g, 17.5 mmol) in tetrahydrofuran (85 mL) was added 1,3-dibromo -5,5-dimethylhydantoin (2.50 g, 8.74 mmol) in four portions over 15 min. The mixture was allowed to stir (−20° C.) for 2 h. The reaction was quenched with the addition saturated aqueous Na2SO3 solution and was allowed to warm to rt. The mixture was extracted with ethyl acetate (3×75 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to dryness. The crude material was purified by MPLC chromatography using a gradient of 50% to 75% ethyl acetate in hexanes to afford 6.29 g (90%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.80 (s, 1 H), 6.58 (s, 1 H), 3.56 (t, 2 H), 2.81 (t, 2 H), 1.72-1.61 (m, 2 H), 1.51-1.42 (m, 2 H), 0.83 (s, 9 H), 0.00 (s, 6 H); ES-MS m/z 399.2 [M+H]+, HPLC RT (min) 3.72.

Workup

customThe reaction was quenched with the addition saturated aqueous Na2SO3 solution
temperatureto warm to rt
extractionThe mixture was extracted with ethyl acetate (3×75 mL)
washThe combined organics were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated to dryness
customThe crude material was purified by MPLC chromatography

Sources & evidence

ORD record: ord-f4d7c158500840d4926ea16fa1c2bf95
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143393B2

Reaction notes

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