Diisopropylethylamine → 2-{4-[(R)-3-Hydroxy-1-(6-methyl-pyridin-3-yl)-propylamino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-5-methyl-benzonitrile

HRID 657795

反応式

HRID 657795 の反応式
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=3[C:14]#[N:15])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:21][C@@H:22]([C:26]1[CH:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=1)[CH2:23][CH2:24][OH:25].C(N(CC)C(C)C)(C)C>C(#N)C>[OH:25][CH2:24][CH2:23][C@@H:22]([NH:21][C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=3[C:14]#[N:15])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1)[C:26]1[CH:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 58103597(R)-3-Amino-3-(6-methylpyridin-3-yl)propan-1-olHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

生成物 1

HCID 250626772-{4-[(R)-3-Hydroxy-1-(6-methyl-pyridin-3-yl)-propylamino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-5-methyl-benzonitrile収率 33.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A reaction mixture of 2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile (60 mg, 0.21 mmol) and (R)-3-amino-3-(6-methylpyridin-3-yl)propan-1-ol (35 mg, 0.21 mmol) in acetonitrile (2 mL) and N,N-diisopropylethylamine (73 μL, 0.42 mmol) was subjected to microwave irradiation at 180° C. for 3 h. The reaction mixture was concentrated and the residue was purified by silica gel column (0-30% MeOH/CH2Cl2) followed by preparative HPLC (100×20.2 mm, C18 column; 20-50% CH3CN-water [10 mM Et2NH]) to yield an off-white solid (29 mg).

後処理

  1. customirradiation at 180° C. for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column (0-30% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-80a7b8ec5c8d48539e324f819317b788
出典データセット
uspto-grants-2011_12
特許番号
US08076345B2

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