Water → 6-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}hexanenitrile

HRID 1926874Notes

Reaction equation

HRID 1926874 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17].Cl[C:19]1[C:20]2[C:27]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[C:26]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:25][C:21]=2[N:22]=[CH:23][N:24]=1.O>CN(C=O)C>[CH3:35][O:34][C:31]1[CH:30]=[CH:29][C:28]([C:27]2[C:20]3[C:19]([NH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:11]#[N:10])=[N:24][CH:23]=[N:22][C:21]=3[O:25][C:26]=2[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 170796-AminohexanenitrileHCID 81531DiisopropylethylamineHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 580169446-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}hexanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 1.15 g (8.9 mmol) DIEA and 0.67 g (5.9 mmol) 6-aminocapronitrile to 1.0 g (3.0 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine in 10 ml DMF and heat for 2 h to 120° C. After cooling, add water to the mixture and extract three times with ethyl acetate. Wash the organic phase with water, with dilute hydrochloric acid and with saturated sodium chloride solution, dry, and concentrate by evaporation. 1.2 g (98% of theor.) of a yellow oil is obtained, and is used as the raw product in further reactions.

Workup

  1. temperatureheat for 2 h to 120° C
  2. temperatureAfter cooling
  3. extractionextract three times with ethyl acetate
  4. washWash the organic phase with water
  5. dry with materialwith dilute hydrochloric acid and with saturated sodium chloride solution, dry
  6. concentrationconcentrate by evaporation
  7. custom1.2 g (98% of theor.) of a yellow oil is obtained

Sources & evidence

ORD record
ord-aa30485bbd614833803655a3f8135312
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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