Triethylamine → (1R,2S,3R,5R)-3-[(6-chloropyrimidin-4-yl)amino]-5-(hydroxymethyl)cyclopentane-1,2-diol

HRID 1677913노트

반응식

HRID 1677913 반응식
Cl.[NH2:2][C@@H:3]1[CH2:7][C@H:6]([CH2:8][OH:9])[C@@H:5]([OH:10])[C@H:4]1[OH:11].[Cl:12][C:13]1[CH:18]=[C:17](Cl)[N:16]=[CH:15][N:14]=1.CCN(CC)CC>CCO>[Cl:12][C:13]1[N:14]=[CH:15][N:16]=[C:17]([NH:2][C@@H:3]2[CH2:7][C@H:6]([CH2:8][OH:9])[C@@H:5]([OH:10])[C@H:4]2[OH:11])[CH:18]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 2734536(1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol Hydrochloride

생성물 1

HCID 59671293(1R,2S,3R,5R)-3-[(6-chloropyrimidin-4-yl)amino]-5-(hydroxymethyl)cyclopentane-1,2-diol수율 90.1%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
150 °C

실험 절차

A mixture of (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (2.00 mg, 1.09 mmol), 4,6-dichloropyrimidine (240. mg, 1.61 mmol) and Et3N (0.380 mL, 2.73 mmol) in EtOH (3.00 mL) was heated to 150° C. for 15 min using MWI. The crude mixture was purified via silica gel chromatography eluting with a gradient of 0 to 15% MeOH in DCM to afford the title compound (255 mg, 90%). LC/MS: Rt=1.13 min, ES+ 260. (AA standard).

후처리

  1. customThe crude mixture was purified via silica gel chromatography
  2. washeluting with a gradient of 0 to 15% MeOH in DCM

출처 및 근거

ORD 기록
ord-6c5834b16db849af88e9dd4fa09dba71
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008307B2

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