Dopamine → 6-{[2-(3,4-Dihydroxy-phenyl)ethylamino]-methyl}-2,4-pteridinediamine

HRID 1272487

반응식

HRID 1272487 반응식
Br.Br[CH2:3][C:4]1[N:5]=[C:6]2[C:11](=[N:12][CH:13]=1)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]2[NH2:15].[OH:16][C:17]1[CH:18]=[C:19]([CH2:24][CH2:25][NH2:26])[CH:20]=[CH:21][C:22]=1[OH:23].C(N(C(C)C)C(C)C)C.C(=O)(O)[O-]>CN(C)C(=O)C>[OH:16][C:17]1[CH:18]=[C:19]([CH2:24][CH2:25][NH:26][CH2:3][C:4]2[N:5]=[C:6]3[C:11](=[N:12][CH:13]=2)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]3[NH2:15])[CH:20]=[CH:21][C:22]=1[OH:23]

참가 물질

6

반응물 4

HCID 681DopamineHCID 769Bicarbonate IonHCID 81531DiisopropylethylamineHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

생성물 1

HCID 184557256-{[2-(3,4-Dihydroxy-phenyl)ethylamino]-methyl}-2,4-pteridinediamine수율 22.6%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 6-bromomethyl-2,4-pteridinediamine hydrobromide (67.3 mg, 0.2003 mmol) in anhydrous N,N dimethylacetamide was added 2-(3,4-dihydroxyphenyl) ethylamine (43.6 mg, 0.23 mmol). Under positive pressure of Argon, iPr2EtN (32.63 ul) was added. The reaction mixture was stirred at 50° C. for 4 hrs and then at Room temperature overnight. The crude product was poured into saturated bicarbonate solution. The resulted precipitate was collected and purified by preparative HPLC. 14.8 mg product was obtained. Yield: 22.6%; 1H NMR (500 MHz, DMSO-d6): δ 2.69242 (b, 4H), 4.03353 (s, 2H), 6.37542–6.39065 (d, J=7.615 Hz, 1H), 6.4851(s, 1H), 6.56632–6.58226 (d, J=7.97 Hz, 1H), 8.80972 (s, 1H); ESI-MS: m/z 328 (M++1)

후처리

  1. customat Room temperature
  2. customovernight
  3. customThe resulted precipitate was collected
  4. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-09e79be0cd044caa97d569d8e6d6e144
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208493B2

연결된 노트

불러오는 중…