Diisopropylethylamine → (4-Methylpiperazin-1-yl)-[3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)phenyl]methanone

HRID 2240121ノート

反応式

HRID 2240121 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.CN(C(ON1N=[N:36][C:31]2C=[CH:33][CH:34]=[N:35][C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:45](N(C(C)C)CC)(C)C.ClC1N=C(CCCN)C2S(=O)(=O)CCC=2N=1>CS(C)=O>[CH3:45][N:35]1[CH2:30][CH2:31][N:36]([C:15]([C:14]2[CH:18]=[CH:19][CH:20]=[C:12]([NH:11][C:4]3[C:5]4[S:10][CH2:9][CH2:8][C:6]=4[N:7]=[C:2]([Cl:1])[N:3]=3)[CH:13]=2)=[O:17])[CH2:33][CH2:34]1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 576001073-(2-Chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acidHCID 86616274(2-chloro-5,5-dioxo-6,7-dihydro-5H-5lambda6-thieno[3,2-d]pyrimidin-4-yl)propylamine

生成物 1

HCID 86616277(4-Methylpiperazin-1-yl)-[3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)phenyl]methanone収率 33%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

0.600 g (1.95 mmol) of 3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)benzoic acid (I), 0.741 g (1.95 mmol) of O-(7-azabenzotriazol-1-yl-)—N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU), and 0.680 mL (3.90 mmol) of diisopropylethylamine are placed in 10 mL of dimethylsulfoxide, then stirred for 0.5 hours at ambient temperature. 0.220 mL (1.95 mmol) of methylpiperazine (II) is added, then the mixture is stirred for 3 hours at ambient temperature. Then the reaction mixture is concentrated by evaporation and the residue is combined with water. Any precipitate formed is suction filtered and dried. The crude product is purified by chromatography through a 50 g silica cartridge with ethyl acetate/methanol 8:2. 0.250 g of product III (33%) is obtained.

後処理

  1. stirringthe mixture is stirred for 3 hours at ambient temperature
  2. concentrationThen the reaction mixture is concentrated by evaporation
  3. customAny precipitate formed
  4. filtrationfiltered
  5. customdried
  6. customThe crude product is purified by chromatography through a 50 g silica cartridge with ethyl acetate/methanol 8:2

出典と根拠

ORDレコード
ord-6b860059b7b540c99d1dc5142e858c0a
出典データセット
uspto-grants-2010_05
特許番号
US07723341B2

反応ノート

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