Benzyl Bromide → HCID 11483653, compound

HRID 2102799Notes

Reaction equation

[CH3:1][C:2]1[S:3][C:4]2[C:13]3[N:12]=[C:11]([NH2:14])[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[N:15]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[NH4+]>C1COCC1>[CH2:26]([NH:14][C:11]1[N:10]=[CH:9][C:8]2[CH2:7][CH2:6][C:5]3[N:15]=[C:2]([CH3:1])[S:3][C:4]=3[C:13]=2[N:12]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To 2-methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-ylamine (100 mg, 0.46 mmol) in dry THF (10 mL), cooled to −78° C., was added LiHMDS (458 μL, 0.46 mmol). The mixture was stirred for 15 min before benzyl bromide (65 μL, 94 mg, 0.55 mmol) was added. The solution was stirred at −78° C. and allowed to warm to room temperature over a period of 16 h. Ammonium chloride solution was added (100 mL) and the product was extracted with CH2Cl2 (3×50 mL). The organic extracts were combined, dried, filtered, and concentrated under vacuum. Flash column chromatography (20% EtOAc:hexane) followed by crystallisation from EtOH gave the title product as orange crystals (28 mg, 20%): mp 152-154° C. 1H-NMR (CDCl3): δ 8.07 (s, 1H, Py-H), 7.40-7.25 (m, 5H, Ph-H), 5.47 (brs, 1H, NH), 4.64 (d, 2H, J 5.8, CH2), 2.98 (m, 4H, CH2—CH2), 2.75 (s, 3H, CH3). MS (ESI+): m/z 309.11 (M+H)+. Anal. (C17H16N4S)C, H, N.

Workup

additionwas added
temperatureto warm to room temperature over a period of 16 h
extractionthe product was extracted with CH2Cl2 (3×50 mL)
customdried
filtrationfiltered
concentrationconcentrated under vacuum
customFlash column chromatography (20% EtOAc:hexane) followed by crystallisation from EtOH

Sources & evidence

ORD record: ord-f9454aa9a7a7431ebc06faab8d90c8b9
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576091B2

Reaction notes

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