Dimethylformamide → 5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

HRID 1365757

反応式

HRID 1365757 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[N:10]=[CH:9][S: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[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:5]2[N:10]=[C:9]([CH:31]=[O:32])[S:8][C:6]=2[N:7]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 576853854-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholineHCID 178418339Butyllithium

生成物 1

HCID 576854055-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 4-(5-chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine 14 (1.75 g, 6.85 mmol) in dry THF 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 uL, 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 was poured onto ice/water yielding a yellow precipitate. This was collected by filtration and air-dried to yield 5-chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde 44.

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 was 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-dafaa15cf0d742e39e6ba4176b20ab22
出典データセット
uspto-grants-2011_02
特許番号
US07893059B2

関連ノート

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