Methyl 4-(2-aminophenyl)butanoate → HCID 25095645, compound

HRID 2189109Notes

Reaction equation

HRID 2189109 reaction equation
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.[CH3:25][O:26][C:27](=[O:38])[CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH2:37]>>[CH3:25][O:26][C:27](=[O:38])[CH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][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:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 237256Methyl 4-(2-aminophenyl)butanoateHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 25095645HCID 25095645, compound

Procedure

Heat 259.8 mg (0.771 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 228 mg of 4-(2-aminophenyl)butanoic acid methyl ester (85% strength, approx. 1.0 mmol) to 150° C. overnight. After cooling, concentrate under reduced pressure, add dichloromethane to the residue and purify the crude product by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 50:1→10:1). The product thus obtained is purified further by preparative RP-HPLC. 33.1 mg (8.7% of theory) of the target product are obtained.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrate under reduced pressure
  3. additionadd dichloromethane to the residue
  4. custompurify the crude product by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 50:1→10:1)
  5. customThe product thus obtained
  6. customis purified further by preparative RP-HPLC
  7. custom33.1 mg (8.7% of theory) of the target product are obtained

Sources & evidence

ORD record
ord-dc6b57e8cb774db69e66252892681d6b
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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