Sodium Bicarbonate → HCID 11231258、化合物

HRID 1836208ノート

反応式

HRID 1836208 の反応式
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3O)[C:6]=2[N:7]=1.O.CC#N.[C:25](OC(C)(C)C(Br)=O)(=[O:27])C.C([O-])(O)=O.[Na+]>C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([O:27][CH3:25])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@H:14]4[O:15][C@@H:12]34)[C:6]=2[N:7]=1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 27247151-Bromocarbonyl-1-methylethyl acetateHCID 11174104HCID 11174104、化合物HCID 18373917Acetonitrile--water (1/1)

生成物 1

HCID 11231258HCID 11231258、化合物収率 115%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a mixture of 2-amino-7-(β-D-ribofuranosyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.8 g, 6.0 mmol) in acetonitrile (80 mL) were added a solution of H2O/CH3CN (1:9, 1.08 mL) and then α-acetoxyisobutyryl bromide (3.5 mL, 24 mmol). After 2 h stirring at room temperature, saturated aqueous NaHCO3 (170 mL) was added and the mixture was extracted with EtOAc (300+200 mL). The combined organic phase was washed with brine (100 mL), dried (Na2SO4) and evaporated to a pale yellow foamy residue. This was suspended in anhydrous MeOH (80 mL) and stirred overnight with 25 mL of DOWEX OH resin (previously washed with anhydrous MeOH). The resin was filtered, washed thoroughly with MeOH and the combined filtrate evaporated to give a pale yellow foam (1.92 g).

後処理

  1. extractionthe mixture was extracted with EtOAc (300+200 mL)
  2. washThe combined organic phase was washed with brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated to a pale yellow foamy residue
  5. stirringstirred overnight with 25 mL of DOWEX OH resin (
  6. washpreviously washed with anhydrous MeOH)
  7. filtrationThe resin was filtered
  8. washwashed thoroughly with MeOH
  9. customthe combined filtrate evaporated

出典と根拠

ORDレコード
ord-424aa4319ca14bd9a899b6268c7dafc6
出典データセット
uspto-grants-2004_08
特許番号
US06777395B2

反応ノート

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