3-Amino-1-propanol → 3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}propan-1-ol

HRID 1926878노트

반응식

HRID 1926878 반응식
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.[NH2:34][CH2:35][CH2:36][CH2:37][OH:38]>CN(C=O)C.C(OCC)(=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:2]([NH:34][CH2:35][CH2:36][CH2:37][OH:38])=[N:7][CH:6]=[N:5][C:4]=3[O:8][C:9]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1

참가 물질

6

반응물 3

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

생성물 1

HCID 580168233-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}propan-1-ol수율 60%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Dissolve 1.00 g (3.0 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine in 10 ml DMF and add 1.15 g (8.9 mmol) DIEA. Add 0.45 g (5.9 mmol) 3-aminopropanol and then heat the mixture over a period of 2 h to 120° C. After cooling, dilute the mixture with ethyl acetate and wash successively with dilute hydrochloric acid and saturated sodium chloride solution. Dry the organic phase over magnesium sulphate and concentrate by evaporation. Purify the residue by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile). 671 mg (60% of theor.) 3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}propan-1-ol is obtained in the form of beige crystals.

후처리

  1. temperatureheat the mixture over a period of 2 h to 120° C
  2. temperatureAfter cooling
  3. washwash successively with dilute hydrochloric acid and saturated sodium chloride solution
  4. dry with materialDry the organic phase over magnesium sulphate
  5. concentrationconcentrate by evaporation
  6. customPurify the residue by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile)

출처 및 근거

ORD 기록
ord-7535b40af0b94dc5aef1e74531262609
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183246B2

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