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

HRID 1926878ノート

反応式

HRID 1926878 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7535b40af0b94dc5aef1e74531262609
出典データセット
uspto-grants-2012_05
特許番号
US08183246B2

反応ノート

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