ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Water → (+)-(1R,3R)-1-(3-hydroxy-cyclopentyl)-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 1243204
ノート
印刷プレビュー

反応式

HRID 1243204 の反応式
C([Si](C)(C)[O:6][C@@H:7]1[CH2:11][CH2:10][C@@H:9]([N:12]2[C:17]3=[N:18][C:19]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:20][CH:21]=[C:16]3[CH2:15][N:14]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:13]2=[O:37])[CH2:8]1)(C)(C)C.O>FC(F)(F)C(O)=O.ClCCl>[OH:6][C@@H:7]1[CH2:11][CH2:10][C@@H:9]([N:12]2[C:17]3=[N:18][C:19]([NH:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[N:20][CH:21]=[C:16]3[CH2:15][N:14]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[C:13]2=[O:37])[CH2:8]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 962WaterHCID 11238111(-)-(1R,3R)-1-[3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

生成物 1

HCID 9910609(+)-(1R,3R)-1-(3-hydroxy-cyclopentyl)-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 6422
Trifluoroacetic acid
溶媒

実験手順

(−)-(1R,3R)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-cyclopentyl]-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (148 mg, 0.27 mmol) (from Example 27e supra) was dissolved at 0° C. in a 25% trifluoroacetic acid in dichloromethane solution (5 mL) that contained water (300 μL). After stirring for 30 minutes the reaction mixture was partitioned between ethyl acetate and 0.5 N aqueous sodium hydroxide. The pH of the aqueous layer was adjusted to 12 via the addition of solid sodium hydroxide. The organic layer was then collected, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by silica gel column chromatography using a 0–100% ethyl acetate in hexanes to 0–40% tetrahydrofuran in ethyl acetate gradient followed by a precipitation out of dichloromethane with excess pentane afforded (+)-(1R,3R)-1-(3-hydroxy-cyclopentyl)-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid. (Yield 92 mg, 86%).

後処理

  1. customwas partitioned between ethyl acetate and 0.5 N aqueous sodium hydroxide
  2. additionThe pH of the aqueous layer was adjusted to 12 via the addition of solid sodium hydroxide
  3. customThe organic layer was then collected
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by silica gel column chromatography
  9. customfollowed by a precipitation out of dichloromethane with excess pentane

出典と根拠

ORDレコード
ord-934846f3585240d4ab68dfddd9553546
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07115740B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート