Water → HCID 86676503, compound

HRID 1854628Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](Br)[N:13]=1.O>C1COCC1>[Br:11][C:12]1[N:13]=[C:14]([NH:1][C:2]2[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=2)[CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 2-amino-4-methylpyrimidine (980 mg, 8.86 mmol) in THF (10 ml) was added dropwise to a cooled suspension of NaH (60% on oil, 1 g, 25.32 mmol) in THF (15 ml) under inert atmosphere. The reaction mixture was heated at 55° C. for 2 hours. The reaction was cooled down to 0° C. and a solution of 2,6-dibromopyridine (2 g, 8.44 mmol) in THF (20 ml) was added. The reaction mixture was heated at 80° C. for 5 hours. The reaction was cooled down to 0° C. and hydrolysed carefully with water (50 ml). After extraction with EtOAc (2×100 ml), the combined extractions were dried over MgSO4. After filtration and evaporation, N-(6-bromopyridin-2-yl)-4-methylpyrimidin-2-amine was obtained and purified dry flash chromatography over SiO2 eluting with DCM/MeOH(1%)/NEt3 (0.5%) (0.846 g, 38%). 1H NMR (300 MHz, DMSO-d6) δ 10.12 (br s, 1H), 8.44 (d, J=5.0 Hz, 1H), 8.36 (d, J=8.3 Hz, 1H), 7.69 (t, J=8.0 Hz, 1H), 7.18 (dd, J=7.6, 0.6 Hz, 1H), 6.91 (d, J=5.0 Hz, 1H), 2.42 (s, 3H).

Workup

temperatureThe reaction was cooled down to 0° C.
temperatureThe reaction mixture was heated at 80° C. for 5 hours
extractionAfter extraction with EtOAc (2×100 ml)
extractionthe combined extractions
dry with materialwere dried over MgSO4
filtrationAfter filtration and evaporation

Sources & evidence

ORD record: ord-a20fb4cea92f47608510a6471ca8197c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962665B2

Reaction notes

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