Phenyl isocyanate → 3-(4-{4-Amino-6-methylthieno[2,3-d]pyrimidin-5-yl}phenyl)-1-phenylurea

HRID 227601Notes

Reaction equation

HRID 227601 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.[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:26]([NH:25][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[O:27])=[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 7672Phenyl isocyanateHCID 65399685-(4-Aminophenyl)-6-methylthieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 65399713-(4-{4-Amino-6-methylthieno[2,3-d]pyrimidin-5-yl}phenyl)-1-phenylureaYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0° C. solution of Example 1E (80 mg, 0.3 mmol) in dichloromethane (4 mL) was treated with phenyl isocyanate (0.037 mL, 0.34 mmol), stirred overnight, and filtered. The filter cake was dried to provide 0.103 g (87%) of the desired product. MS (CI) m/e 376 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.89 (s, 1H); 8.75 (s, 1H); 8.26 (s, 1H); 7.63 (d, J=8.7 Hz, 2H); 7.47 (d, J=8.7 Hz, 2H); 7.33-7.26 (m, 4H); 6.99 (t, J=7.5 Hz, 1H); 2.30 (s, 3H); Anal. Calcd. for C20H17N5OS.0.1CH2Cl2: C, 62.88; H, 4.52; N, 18.24. Found: C, 62.85; H, 4.64; N, 18.15.

Workup

  1. filtrationfiltered
  2. customThe filter cake was dried

Sources & evidence

ORD record
ord-cee1a024016749b2b3ac592d3b91d6bc
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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