Dimethylformamide → 2-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

HRID 41889

反応式

HRID 41889 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C([Li])CCC.CCCCCC.CN([CH:31]=[O:32])C>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][C:9]([CH:31]=[O:32])=[CH:8][C:6]=2[N:7]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 202849712-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde収率 77%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 4 (1.75 g, 6.85 mmol) in dry THF (40 mL) at −78° C. was added a 2.5M solution of n-butyllithium (nBuLi) in hexane (3.3 mL, 1.2 eq.). After stirring for 1 h, dry DMF (796 μL, 1.5 eq.) was added. The reaction mixture was stirred for 1 h at −78° C. and then warmed slowly to room temperature. After a further 2 h at room temperature the reaction mixture poured onto ice/water yielding a yellow precipitate. This was collected by filtration and air-dried to yield 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde 10 (1.50 g, 77%). 1H NMR (400 MHz, d6-DMSO) 3.76 (4H, t, J=4.9), 3.95 (4H, t, J=4.9), 8.28 (1H, s), 10.20 (1H, s).

後処理

  1. stirringThe reaction mixture was stirred for 1 h at −78° C.
  2. additionAfter a further 2 h at room temperature the reaction mixture poured onto ice/water yielding a yellow precipitate
  3. filtrationThis was collected by filtration
  4. customair-dried

出典と根拠

ORDレコード
ord-76acf974a50b4dacafebf9f1ea33440f
出典データセット
uspto-grants-2013_09
特許番号
US08536161B2

関連ノート

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