Potassium Carbonate → HCID 86670105、化合物

HRID 2169557ノート

反応式

HRID 2169557 の反応式
Br[C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:18][CH:17]3[CH2:19][O:20][CH2:21][CH2:22][N:16]3[C:15]3[N:14]=[C:13]([Cl:23])[N:12]=[CH:11][C:10]2=3)[CH:5]=[CH:4][CH:3]=1.[C:24]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:23][C:13]1[N:12]=[CH:11][C:10]2[N:9]([CH2:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:24])[N:7]=3)[CH2:18][CH:17]3[CH2:19][O:20][CH2:21][CH2:22][N:16]3[C:15]=2[N:14]=1

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 866701045-((6-Bromopyridin-2-yl)methyl)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

生成物 1

HCID 86670105HCID 86670105、化合物収率 57.4%

試薬・触媒・溶媒 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a 10 mL vial was added 5-((6-bromopyridin-2-yl)methyl)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x27, 75 mg, 0.189 mmol), K2CO3 (52.3 mg, 0.378 mmol), PdCl2(dppf) (13.83 mg, 0.019 mmol) and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.053 mL, 0.378 mmol) in dioxane (2 mL) and H2O (0.4 mL) to give an orange suspension. The reaction vial was sealed, heated to 100° C., and stirred overnight. The reaction mixture was then diluted with ethyl acetate and washed with aqueous saturated NH4Cl (3×10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give crude product, which was loaded onto an ISCO® silica gel cartridge (4 g) and eluted using an ethyl acetatehexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a yellow solid (36 mg, 57%). 1H NMR (400 MHz, DMSO-d6) δ 2.45 (s, 3 H), 2.92-3.05 (m, 1 H), 3.12-3.27 (m, 2 H), 3.40-3.52 (m, 2 H), 3.61-3.74 (m, 1 H), 3.85-4.00 (m, 2 H), 4.18-4.28 (m, 1 H), 4.35-4.58 (m, 2 H), 7.10-7.17 (m, 2 H), 7.30 (s, 1 H), 7.60-7.68 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C16H18ClN5O, 331.12; found 331.2.

後処理

  1. customto give an orange suspension
  2. customThe reaction
  3. customvial was sealed
  4. washwashed with aqueous saturated NH4Cl (3×10 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give crude product, which
  9. washeluted
  10. customThe product was collected
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-90636f3c450641649f3ac24ce9c887cb
出典データセット
uspto-grants-2015_06
特許番号
US09045496B2

反応ノート

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