Phenyl isocyanate → HCID 59514570, compound

HRID 1159660Notes

Reaction equation

HRID 1159660 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[N:12]=[C:11]([Cl:13])[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:9]([N:19]([CH2:21][C:22]([NH:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:23])[CH3:20])[N:8]=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.CCOC(C)=O>CN(C=O)C>[NH:38]([C:39]([NH:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[N:12]=[C:11]([Cl:13])[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:9]([N:19]([CH2:21][C:22]([NH:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:23])[CH3:20])[N:8]=2)=[CH:4][CH:3]=1)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8857Ethyl AcetateHCID 59514491HCID 59514491, compound

Product 1

HCID 59514570HCID 59514570, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl {2-(4-aminobenzyl)-4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl](methyl)-amino]pyrimidin-5-yl}acetate (0.050 g, 0.11 mmol) in DMF (2 mL) was treated with phenyl isocyanate (0.022 mL, 0.20 mmol). After stirring at room temperature for 18 hours, EtOAc was added and the organic phase was washed with 8% NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product thus obtained was triturated with CH2Cl2 and diisopropyl ether to give methyl {2-{4-[(anilinocarbonyl)amino]benzyl}-4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl](methyl)amino]pyrimidin-5-yl}acetate (0.055 g, 87% yield) as a white powder.

Workup

  1. washthe organic phase was washed with 8% NaHCO3 and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product thus obtained
  6. customwas triturated with CH2Cl2 and diisopropyl ether

Sources & evidence

ORD record
ord-6dcffee3fdce4d4f8511a3f2a66b2819
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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