Triethylamine → 4-(4-Benzyloxy-3-chloro-phenylamino)-6-chloro-pyrimidine-5-carbonitrile

HRID 384726

Reaktionsgleichung

Reaktionsgleichung von HRID 384726
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.CCN(CC)CC.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][C:27]=1[Cl:33])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1.CCOC(C)=O>[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:2]2[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=2)=[CH:28][C:27]=1[Cl:33])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 5993714,6-Dichloropyrimidine-5-carbonitrileHCID 12682854-Benzyloxy-3-chloroaniline

Produkt 1

HCID 590118834-(4-Benzyloxy-3-chloro-phenylamino)-6-chloro-pyrimidine-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4,6-dichloro-pyrimidine-5-carbonitrile Compound 2a (82 mg, 0.47 mmol), Et3N (0.13 mL, 0.94 mmol) and 4-benzyloxy-3-chloro-phenylamine Compound 2b (110 mg, 0.47 mmol) in THF (4.7 mL) was stirred at 25° C. for 3 hours. The reaction mixture was diluted with EtOAc (50 mL), washed with water (1×50 mL) and concentrated to afford 4-(4-benzyloxy-3-chloro-phenylamino)-6-chloro-pyrimidine-5-carbonitrile Compound 2c (175 mg, 100%) as an off-white solid; 1H NMR (300 MHz, CD3OD) δ 8.42 (s, 1H), 7.63 (s, 1H), 7.52-7.40 (m, 7H), 7.12 (m, 1H), 5.22 (s, 2H), 5.19 (s, 2); MS (ESI) m/z: 373 (MH+).

Aufarbeitung

  1. washwashed with water (1×50 mL)
  2. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-93717b372a4b4408a774307df9439b68
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367825B2

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