Diisopropylethylamine → (R)-3-(6-Methyl-pyridin-3-yl)-3-[6-(5-methyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ylamino]-propan-1-ol

HRID 241883

Reaktionsgleichung

Reaktionsgleichung von HRID 241883
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=3)[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:19][C@@H:20]([C:24]1[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=1)[CH2:21][CH2:22][OH:23].C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:30][C:27]1[N:26]=[CH:25][C:24]([C@H:20]([NH:19][C:2]2[C:3]3[CH2:11][N:10]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=4)[CH2:9][CH2:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:21][CH2:22][OH:23])=[CH:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 58103597(R)-3-Amino-3-(6-methylpyridin-3-yl)propan-1-olHCID 593464574-Chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine

Produkt 1

HCID 25032351(R)-3-(6-Methyl-pyridin-3-yl)-3-[6-(5-methyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ylamino]-propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A reaction mixture of 4-chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine (35 mg, 0.14 mmol) and (R)-3-amino-3-(6-methylpyridin-3-yl)propan-1-ol (15 mg, 0.090 mmol) in acetonitrile (1.5 mL) and N,N-diisopropylethylamine (31 μL, 0.18 mmol) was subjected to microwave irradiation at 180° C. for 2 h. The reaction mixture was concentrated and purified by semi-prep HPLC ((100×20.2 mm, C18 column; 30-60% CH3CN-water [10 mM Et2NH]) to give a light yellow foam. LC-MS: 391.4 [M+H]+.

Aufarbeitung

  1. customirradiation at 180° C. for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by semi-prep HPLC ((100×20.2 mm, C18 column; 30-60% CH3CN-water [10 mM Et2NH])
  4. customto give a light yellow foam

Quellen und Nachweise

ORD-Eintrag
ord-9eda7b5becdd41dd858552b24bbbe4f1
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653091B2

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