Phenyl isocyanate → 1-(4-{2-[(5,6-Diphenylfuro[2,3-D]pyrimidin-4-Yl)amino]ethyl}phenyl)-3-Phenylurea

HRID 1095472Notes

Reaction equation

HRID 1095472 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH2:7][NH:8][C:9]2[C:10]3[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[CH:4][CH:3]=1.[C:32]1([N:38]=[C:39]=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(#N)C>[C:18]1([C:17]2[C:10]3[C:9]([NH:8][CH2:7][CH2:6][C:5]4[CH:30]=[CH:31][C:2]([NH:1][C:39]([NH:38][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[O:40])=[CH:3][CH:4]=4)=[N:14][CH:13]=[N:12][C:11]=3[O:15][C:16]=2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 46855043N-(4-aminophenethyl)-5,6-diphenylfuro[2,3-d]pyrimidin-4-amine

Product 1

HCID 444701721-(4-{2-[(5,6-Diphenylfuro[2,3-D]pyrimidin-4-Yl)amino]ethyl}phenyl)-3-PhenylureaYield 95.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(4-aminophenethyl)-5,6-diphenylfuro[2,3-d]pyrimidin-4-amine (0.195 g) in acetonitrile (10 mL) was added phenyl isocyanate (0.063 g). After stirring at room temperature for 16 h, the reaction mixture was concentrated and the residue was partitioned between water and ethyl acetate. The organic layer was concentrated and the crude compound was purified by silica gel column chromatography using a mixture of hexanes:ethyl acetate (1:1), to give 1-(4-(2-(5,6-diphenylfuro[2,3-d]pyrimidin-4-ylamino)ethyl)phenyl)-3-phenylurea (0.240 g, 95%). 1H-NMR (CDCl3, 300 MHz): δ 8.42 (s, 1 H), 7.58 (brs, 1 H), 7.43-7.39 (m, 5 H), 7.33-7.18 (m, 11 H), 7.03-6.98 (m, 1 H), 6.86-6.83 (m, 2 H), 4.67 (t, 1 H), 3.63 (q, 2 H), 2.66 (t, 2 H). LC-MS (ESI) m/z 526.2 (M+H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was partitioned between water and ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customthe crude compound was purified by silica gel column chromatography
  5. additiona mixture of hexanes:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-cf14d2f6df3a4d1b909dfff382d0f52e
Source dataset
uspto-grants-2012_03
Patent number
US08138194B2

Reaction notes

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