Sodium Carbonate → 6-Benzyl-2-(2,6-dimethylphenyl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80763

Reaktionsgleichung

Reaktionsgleichung von HRID 80763
[CH2:1]([N:8]1[CH2:20][CH2:19][C:11]2[N:12]=[C:13](Cl)[N:14]=[C:15]([O:16][CH3:17])[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH2:20][CH2:19][C:11]2[N:12]=[C:13]([C:23]3[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:22]=3[CH3:21])[N:14]=[C:15]([O:16][CH3:17])[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 5833222,6-Dimethylphenylboronic acidHCID 866902516-Benzyl-2-chloro-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Produkt 1

HCID 712447526-Benzyl-2-(2,6-dimethylphenyl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of 6-benzyl-2-chloro-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (6.52 g, 22.5 mmol) and 2,6-dimethylphenylboronic acid (3.90 g, 26.0 mmol) in 1,2-dimethoxyethane (175 mL), was added 2 M aqueous Na2CO3 (35.2 mL, 70.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.751 g, 0.651 mmol). The reaction was flushed with nitrogen, then heated to 100° C. for 48 h. The reaction mixture was cooled to r.t., then ethyl acetate and brine were added. The aqueous layer was extracted by ethyl acetate twice. The combined ethyl acetate layers were dried over Na2SO4, filtered, and concentrated. The resulting residue was purified via silica gel FCC (0-40% EtOAc/heptane) to give 6-benzyl-2-(2,6-dimethylphenyl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. 1H NMR (400 MHz, CD2Cl2) δ ppm 7.23-7.46 (m, 5 H), 7.12-7.21 (m, 1 H), 7.04-7.10 (m, 1 H), 6.97 (d, J=7.6 Hz, 1 H), 3.94 (d, J=10.1 Hz, 3 H), 3.73 (d, J=16.4 Hz, 2 H), 3.36-3.56 (m, 2 H), 2.91 (d, J=4.8 Hz, 1 H), 2.84 (br. s., 2 H), 2.77 (t, J=5.4 Hz, 1 H), 2.35 (s, 3 H), 2.08 (s, 3 H). MS (ESI+) m/z 360.3 (M+H)+.

Aufarbeitung

  1. customThe reaction was flushed with nitrogen
  2. temperatureThe reaction mixture was cooled to r.t.
  3. additionethyl acetate and brine were added
  4. extractionThe aqueous layer was extracted by ethyl acetate twice
  5. dry with materialThe combined ethyl acetate layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified via silica gel FCC (0-40% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-636748cbbf4246519be9598d0b0d21d1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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