5-Amino-4,6-dichloropyrimidine → 6-Chloro-N4-[1-(3,5-diisopropoxy-benzyl)-piperidin-4-yl]-pyrimidine-4,5-diamine

HRID 2426546노트

반응식

HRID 2426546 반응식
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[CH:10]([O:13][C:14]1[CH:15]=[C:16]([CH:25]=[C:26]([O:28][CH:29]([CH3:31])[CH3:30])[CH:27]=1)[CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]1)([CH3:12])[CH3:11]>C(N(C(C)C)C(C)C)C.C(#N)C>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:24][CH:21]2[CH2:22][CH2:23][N:18]([CH2:17][C:16]3[CH:15]=[C:14]([O:13][CH:10]([CH3:11])[CH3:12])[CH:27]=[C:26]([O:28][CH:29]([CH3:31])[CH3:30])[CH:25]=3)[CH2:19][CH2:20]2)[C:7]=1[NH2:8]

참가 물질

5

반응물 2

HCID 794345-Amino-4,6-dichloropyrimidineHCID 592103701-(3,5-Diisopropoxy-benzyl)-piperidin-4-ylamine2회

생성물 1

HCID 866185376-Chloro-N4-[1-(3,5-diisopropoxy-benzyl)-piperidin-4-yl]-pyrimidine-4,5-diamine수율 20%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 81531Diisopropylethylamine용매

실험 절차

A solution of 4,6-dichloro-pyrimidin-5-ylamine (19.7 mg, 0.12 mmol, 1.0 equiv; commercially available) and 1-(3,5-diisopropoxy-benzyl)-piperidin-4-ylamine (46.0 mg, 0.15 mmol, 1.25 equiv; intermediate A3) in N-ethyl diisopropylamine (1.0 mL) and acetonitril (1.0 mL) was heated by microwave irradiation to 160° C. for 20 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 10.6 mg (20%) of the title compound. MS (ISP): 434.3 [M+H]+.

후처리

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

출처 및 근거

ORD 기록
ord-49a1894631f44386924bbbfc2a93bacc
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968568B2

반응 노트

불러오는 중…