Tetrahydro-4H-pyran-4-one → 4-(6-((2H-pyran-4(3H,5H,6H)-ylidene)methyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine

HRID 1043639ノート

反応式

HRID 1043639 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[N:11]=[C:10]([CH2:12]P(=O)(OC)OC)[CH:9]=[CH:8][C:6]=2[N:7]=1.C([N-]C(C)C)(C)C.[Li+].[O:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1>C1COCC1>[O:33]1[CH2:38][CH2:37][C:36](=[CH:12][C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)[C:5]=3[N:11]=2)[CH2:35][CH2:34]1

参加物

5

反応物 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 2724682Lithium diisopropylamideHCID 58405032Dimethyl (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylphosphonate

生成物 1

HCID 584050234-(6-((2H-pyran-4(3H,5H,6H)-ylidene)methyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a suspension of dimethyl (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methylphosphonate from Example 117 (0.45 g) in anhydrous THF (6 mL) at 0° C. was added 2.0 M of lithium diisopropylamide in tetrahydrofuran (1.5 eq). The resulting solution was allowed to warm to RT before adding a solution of dihydro-2H-pyran-4(3H)-one (1.5 eq) in anhydrous THF (3 mL). The reaction mixture was stirred at room temperature for 1 h, then partitioned between brine and Ethyl Acetate. The organic layer was isolated, dried (MgSO4), concentrated and recrystallized from methanol. The light yellow solid was filtered and collected to give 0.36 g of 4-(6-((2H-pyran-4(3H,5H,6H)-ylidene)methyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine as a light yellow solid.

後処理

  1. custompartitioned between brine and Ethyl Acetate
  2. customThe organic layer was isolated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customrecrystallized from methanol
  6. filtrationThe light yellow solid was filtered
  7. customcollected

出典と根拠

ORDレコード
ord-7e9050b21835481eaf1804f6363ad662
出典データセット
uspto-grants-2013_10
特許番号
US08563540B2

反応ノート

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