Diphenyl N-Cyanocarbonimidate → HCID 178435033, compound

HRID 227623Notes

Reaction equation

HRID 227623 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH3:18])=[CH:4][CH:3]=1.[CH:19]1[CH:24]=[CH:23][C:22]([O:25][C:26](OC2C=CC=CC=2)=[N:27][C:28]#[N:29])=[CH:21][CH:20]=1>CN(C=O)C>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:26](=[N:27][C:28]#[N:29])[O:25][C:22]4[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=4)=[CH:7][CH:6]=3)=[C:9]([CH3:18])[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 65399685-(4-Aminophenyl)-6-methylthieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 178435033HCID 178435033, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 1E (0.4 g, 1.56 mmol) and diphenyl cyanocarbonimidate (0.372 g, 1.56 mmol) in DMF (10 mL) was heated to 90° C. for 2 days, cooled to room temperature, quenched with water, and filtered. The filter cake was suspended in ethanol and filtered. The filtrate was concentrated and purified by flash column chromatography on silica gel with 5 to 8% methanol/dichloromethane to provide the desired product (150 mg). MS(ESI(+)) m/e 401(M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 11.06 (s, 1H); 8.27 (s, 1H); 7.67 (d, J=8.4 Hz, 2H); 7.50-7.43 (m, 4H); 7.36-7.29 (m, 3H); 2.29 (s, 3H).

Workup

  1. customquenched with water
  2. filtrationfiltered
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by flash column chromatography on silica gel with 5 to 8% methanol/dichloromethane

Sources & evidence

ORD record
ord-9520e5fdaa1a4270bd0a965a1abba787
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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