338
Russ.Chem.Bull., Int.Ed., Vol. 61, No. 2, February, 2012
Komkov et al.
Table 2. The 1H NMR spectra of pyrimidinethiones 9b—i, methylsulfanylpyrimidines 4a—i, and methylsulfonylpyrimidines 14a—f
in CDCl3
Comꢀ
pound
(J/Hz)
4а
4b
4c
4d
4e*
4f
2.48 (s, 3 H, MеCO); 2.63 (s, 3 H, SMе); 3.64 (m, 4 H, 2 CН2N); 3.81 (m, 4 H, 2 СН2O); 7.50 (m, 3 H, Ph);
8.47 (m, 2 H, Ph)
2.32 (s, 3 H, NMе); 2.46 (s, 3 H, MеCO); 2.51 (m, 4 H, 2 СН2N); 2.64 (s, 3 H, SMе); 3.71 (m, 4 H, 2 СН2N);
7.49 (m, 3 H, Ph); 8.47 (m, 2 H, Ph)
2.52 (s, 3 H, MеCO); 2.68 (s, 3 H, SMе); 3.18 (m, 4 H, 2 СН2N); 3.78 (s, 3 H, OMe); 3.85 (m, 4 H, 2 СН2N);
6.88 (m, 4 H, C6H4); 7.50 (m, 3 H, Ph); 8.49 (m, 2 H, Ph)
2.50 (s, 3 H, MеCO); 2.65 (s, 3 H, SMе); 3.21 (m, 4 H, 2 СН2N); 3.82 (m, 4 H, 2 СН2N); 6.91 (m, 2 H, C6H4);
6.98 (m, 2 H, C6H4); 7.49 (m, 3 H, Ph); 8.48 (m, 2 H, Ph)
2.32 (s, 6 H, 2 Mе); 2.72 and 2.80 (both s, 6 H, СОMе and SMе); 6.81 (s, 1 H, рꢀHC H ); 7.45 (m, 5 H, mꢀHPh
,
6
3
pꢀHPh and oꢀHC H ); 8.48 (m, 2 H, оꢀHPh); 11.35 (br.s, 1 Н, NH)
6
3
2.78 and 2.87 (both s, 6 H, СОMе and SMе); 7.12 (d, 1 H, рꢀHC H , J = 7.8); 7.32 (t, 1 H, mꢀHC H , J = 7.8);
7.51 (m, 4 H, mꢀHPh, pꢀHPh and oꢀHC H ); 8.02 (s, 1 H, оꢀHC H6);48.48 (m, 2 H, оꢀHPh); 11.53 (br.s, 1 Н, NH)
6
4
4
6
4
4g
4h
4i
2.79 and 2.88 (both s, 6 H, СОMе and 6SMе); 7.41 (d, 1 H, рꢀHC H , J = 7.8); 7.49 (m, 4 H, mꢀHPh, pꢀHPh and mꢀHC H );
7.72 (d, 1 H, oꢀHC H , J = 7.8); 8.40 (s, 1 H, оꢀHC H ); 8.46 (m, 62 H, оꢀHPh); 11.63 (br.s, 1 Н, NH)
4
6
4
2.73 and 2.80 (both s, 6 H, СОMе and SMе); 4.90 6(d4, 2 H, CH2, J = 5.0); 7.25—7.54 (m, 8 H, 3 HPh and 5 HPhCH );
6
4
2
8.48 (m, 2 H, Ph); 9.88 (br.t, 1 Н, NH)
0.97 (t, 3 H, MеСН2, J = 7.2); 1.45 (m, 2 H, СН2); 1.68 (m, 2 H, СН2); 2.72 and 2.78 (both s, 6 H, СОMе and SMе);
3.69 (m, 2 H, СН2N); 7.49 (m, 3 H, Ph); 8.49 (m, 2 H, Ph); 9.51 (br.t, 1 Н, NH)
2.31 (s, 3 H, NMе); 2.51 (m, 4 H, 2 СН2N); 2.82 (s, 3 H, MеCO); 3.70 (m, 4 H, 2 СН2N); 7.58 (m, 3 H, Ph);
7.97 (m, 2 H, Ph); 10.02 (br.s, 1 Н, NH)
2.85 (s, 3 H, MеCO); 3.18 (m, 4 H, 2 СН2N); 3.80 (s, 3 H, OMe); 3.85 (m, 4 H, 2 СН2N); 6.88 (m, 4 H, C6H4);
7.58 (m, 3 H, Ph); 7.98 (m, 2 H, Ph); 10.25 (br.s, 1 Н, NH)
9b
9c
9d
9e
9f
2.85 (s, 3 H, MеCO); 3.21 (m, 4 H, 2 СН2N); 3.82 (m, 4 H, 2 СН2N); 6.85 (m, 2 H, C6H4); 6.94 (m, 2 H, C6H4);
7.60 (m, 3 H, Ph); 7.98 (m, 2 H, Ph); 10.32 (br.s, 1 Н, NH)
2.32 (s, 6 H, 2 Mе); 3.32 (s, 3 H, СОMе); 6.87 (s, 1 H, рꢀHC H ); 7.21 (s, 2 H, oꢀHC H ); 7.56 (t, 2 Н, mꢀHPh, J = 7.8);
6
7.65 (t, 1 Н, рꢀHPh, J = 7.8); 7.91 (m, 2 H, оꢀHPh); 10.28 (br6.s,31 Н, NH); 12.43 (br.s, 31 Н, NHC6H3)
3.04 (s, 3 H, СОMе); 7.21 (d, 1 H, рꢀHC H , J = 7.8); 7.31 (t, 1 H, mꢀHC H , J = 7.8); 7.40 (d, 1 H, oꢀHC H , J = 7.8);
6
4
6
4
7.59 (t, 2 H, mꢀHРh, J = 7.8); 7.66 (t, 1 H, pꢀHРh, J = 7.8); 7.81 (s, 1 H, оꢀHC H ); 7.99 (d, 2 H, оꢀHPh, J 6= 47.8);
6
4
10.31 (br.s, 1 Н, NH); 12.64 (br.s, 1 Н, NHC6H4)
9g
9h
9i
3.04 (s, 3 H, СОMе); 7.41—7.74 (m, 6 H, mꢀHPh, pꢀHPh, oꢀHC H , mꢀHC H , рꢀHC H ); 7.99 (d, 2 H, оꢀHPh, J = 7.8);
6 4 4 6 4
8.20 (s, 1 H, оꢀHC H ); 10.38 (br.s, 1 Н, NH); 12.75 (br.s, 1 Н, NHC6H4) 6
6
3.00 (s, 3 H, СОMе)4; 4.91 (d, 2 H, CH2, J = 5.0); 7.32 (m, 5 H, PhCH2); 7.56 (t, 2 H, mꢀHРh, J = 7.8);
7.63 (t, 1 H, рꢀHРh, J = 7.8); 7.99 (d, 2 H, оꢀHPh, J = 7.8); 10.22 (br.s, 1 Н, NH); 11.10 (br.t, 1 Н, NHCH2)
0.96 (t, 3 H, MеСН2, J = 7.2); 1.42 (m, 2 H, СН2); 1.69 (m, 2 H, СН2); 2.98 (s, 3 H, СОMе); 3.68 (m, 2 H, СН2N);
7.56 (t, 2 H, mꢀHРh, J = 7.8); 7.62 (t, 1 H, рꢀHРh, J = 7.8); 8.01 (d, 2 H, оꢀHPh, J = 7.8); 10.11 (br.s, 1 Н, NH);
10.78 (br.t, 1 Н, NHCH2)
14а
14b
2.79 (s, 3 H, MеCO); 3.40 (s, 3 H, SО2Mе); 6.62 (br.s, 2 H, NН2); 7.50 (m, 3 H, Ph); 8.35 (d, 2 H, Ph, J = 7.8)
2.38 (s, 6 H, 2 Mе); 2.84 (s, 3 H, MеCO); 3.41 (s, 3 H, SO2Me); 6.87 (s, 1 H, pꢀHC H ); 7.31 (s, 2 H, oꢀHC H );
6
3
6
3
7.51 (m, 3 H, Ph); 8.38 (d, 2 H, Ph, J = 7.8); 8.91 (br.s, 1 Н, NH)
2.88 (s, 3 H, MеCO); 3.42 (s, 3 H, SО2Mе); 7.19 (d, 1 H, pꢀHC H , J = 7.8); 7.36 (t, 1 H, mꢀHC H , J = 7.8);
14c
6
4
7.45 (d, 1 H, оꢀHC H , J = 7.8); 7.53 (m, 3 H, mꢀHPh, рꢀHРh); 7.941 (s, 1 H, оꢀHC H ); 8.48 (d, 26H, оꢀHPh, J = 7.8);
6
6
4
9.12 (br.s, 1 Н, NH) 4
14d
2.91 (s, 3 H, MеCO); 3.45 (s, 3 H, SО2Mе); 7.43—7.62 (m, 5 H, рꢀHC H , mꢀHC H , mꢀHPh, рꢀHРh);
6 4 6 4
7.66 (d, 1 H, оꢀHC H , J = 7.8); 8.31 (s, 1 H, оꢀHC H ); 8.39 (d, 2 H, оꢀHPh, J = 7.8); 9.30 (br.s, 1 Н, NH)
6
4
6
14e**
2.79 (s, 3 H, MеСО); 3.39 (s, 3 H, SО2Mе); 4.86 (d, 42 H, CH2, J = 6.0); 7.32 (m, 1 H, рꢀHPhCH ); 7.38 (m, 4 Н,
2
оꢀHPhCH , mꢀHPhCH ); 7.43 (br.t, 1 Н, NH); 7.50 (t, 2 H, mꢀHPh, J = 7.8); 7.55 (t, 1 H, рꢀHPh, J = 7.8);
2
2
8.40 (d, 2 H, оꢀHPh, J = 7.8)
14f
0.98 (t, 3 H, MеСН2, J = 7.2); 1.44 (m, 2 H, СН2); 1.69 (m, 2 H, СН2); 2.78 (s, 3 H, СОMе); 3.39 (s, 3 H, SО2Mе);
3.67 (m, 2 H, СН2N); 7.10 (br.t, 1 H, NH); 7.51 (m, 3 H, Ph); 8.40 (d, 2 H, Ph, J = 7.8)
* Here and in the 1H NMR spectra reported below, positions of the protons in disubstituted and trisubstituted benzene rings are given
with respect to the carbon atom bonded the nitrogen atom.
** The spectrum was recorded on a spectrometer with the operational frequency of 600 MHz.