m-Tolylisothiocyanate → Thienopyrimidine deriv. 65

HRID 227626

Reaction equation

HRID 227626 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.[CH3:19][C:20]1[CH:21]=[C:22]([N:26]=[C:27]=[S:28])[CH:23]=[CH:24][CH:25]=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:27]([NH:26][C:22]4[CH:23]=[CH:24][CH:25]=[C:20]([CH3:19])[CH:21]=4)=[S:28])=[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 69304m-TolylisothiocyanateHCID 65399685-(4-Aminophenyl)-6-methylthieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 6539974Thienopyrimidine deriv. 65Yield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 1E (60 mg, 0.23 mmol) and 3-methylphenyl isothiocyanate in DMF (2 mL) was stirred at room temperature, for 48 hours, quenched with water, and filtered. The filter cake was dried to provide the desired product (75 mg, 80%). MS(ESI(+)) m/e 406 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 9.96 (s, 1H); 9.84 (s, 1H); 8.27 (s, 1H); 7.65 (d, J=8.4 Hz, 2H); 7.35 (d, J=8.4 Hz, 2H); 7.30-7.18 (m, 3H); 6.97 (d, J=6.9 Hz, 1H); 2.30 (s, 6H).

Workup

  1. customquenched with water
  2. filtrationfiltered
  3. customThe filter cake was dried

Sources & evidence

ORD record
ord-e9e43410ddf145fcad3dadf6b8e5628a
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Linked notes

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