S. Chercheja et al. / Tetrahedron 67 (2011) 3839e3845
3843
2961; 1608; 1568; 1452, 1433, 1387, 1172, 786 cmꢁ1
;
1H NMR
3.89 (3H, s, OCH3), 2.99 (2H, t, J¼7.8 Hz, CH2Ar), 2.74 (2H, t, J¼7.4 Hz,
CH2Ar), 2.20e2.12 (2H, m, CH2CH2Ar); 13C NMR (100.6 MHz, CDCl3)
(400 MHz, DMSO-d6) 8.02e8.00 (2H, m, ArH), 6.58e6.56 (2H, m,
d
ArH), 6.41 (2H, br s, NH2), 5.37 (2H, br s, NH2), 2.74 (2H, t, J¼7.6 Hz,
CH2Ar), 2.64 (2H, t, J¼7.2 Hz, CH2Ar), 2.01e1.94 (2H, m, CH2CH2Ar);
d 173.2 (C), 163.5 (C), 159.7 (C), 159.3 (C), 140.0 (C), 129.2 (CH), 120.5
(CH), 116.3 (CH), 114.0 (C), 112.6 (CH), 55.3 (CH3), 34.2 (CH2), 26.7
(CH2), 21.6 (CH2); HRMS (ES) exact mass calcd for C14H16N3O
[MþH]þ: 242.1293, found: 242.1297.
13C NMR (100.6 MHz, DMSO-d6)
d 171.1 (C), 162.6 (C), 159.8 (C),
150.2 (C), 128.8 (2ꢂ CH), 126.1 (C), 113.0 (2ꢂ CH), 111.8 (C), 33.7
(CH2), 26.8 (CH2), 21.1 (CH2); HRMS (ES) exact mass calcd for
C13H15N4 [MþH]þ: 227.1297, found: 227.1287.
4.2.14. 2-Naphthalen-2-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-
ylamine (5o). The title compound was prepared according to gen-
4.2.10. 2-(4-Dimethylaminophenyl)-6,7-dihydro-5H-cyclo-
pentapyrimidin-4-ylamine (5j). The title compound was prepared
according to a modification of general procedure A using 4-dime-
thylaminobenzonitrile (190 mg, 1.30 mmol) for an increased re-
action time of 20 h and purified by flash chromatography (0%
eral procedure A using naphthalene-2-carbonitrile (199 mg,
1.30 mmol) and purified by flash chromatography (0% EtOAc/
cyclohexane/100% EtOAc/cyclohexane) to give a white solid
(288 mg, 85%). Mp 176e178 ꢀC; IR (film) 3325 (NH), 3183, 2957,
1613, 1568, 1451, 1433, 1400, 788 cmꢁ1; 1H NMR (400 MHz, DMSO-
EtOAc/cyclohexane/100%
EtOAc/cyclohexane/20%
MeOH/
d6)
d
8.85 (1H, s, ArH), 8.45 (1H, dd, J¼8.5, 1.5 Hz, ArH), 8.04e8.02
CH2Cl2) to give a white solid (68 mg, 21%). Mp 253e256 ꢀC
(decomp.); IR (film) 3484, 3298 (NH), 3183, 2905, 1604, 1572, 1381,
(1H, m, ArH), 7.96e7.92 (2H, m, ArH), 7.55e7.52 (2H, m, ArH), 6.75
(2H, br s, NH2), 2.85 (2H, t, J¼7.7 Hz, CH2Ar), 2.71 (2H, t, J¼7.3 Hz,
CH2Ar), 2.08e2.00 (2H, m, CH2CH2Ar); 13C NMR (100.6 MHz,
1176, 826, 783 cmꢁ1; 1H NMR (400 MHz, DMSO-d6)
d 8.14e8.12 (2H,
m, ArH), 6.73e6.70 (2H, m, ArH), 6.48 (2H, br s, NH2), 2.96 (6H, s,
N(CH3)2), 2.76 (2H, t, J¼7.7 Hz, CH2Ar), 2.65 (2H, t, J¼7.4 Hz, CH2Ar),
2.02e1.95 (2H, m, CH2CH2Ar); 13C NMR (100.6 MHz, DMSO-d6)
DMSO-d6) d 171.4 (C), 163.2 (C), 161.8 (C), 160.2 (C), 136.0 (C), 133.7
(C), 132.8 (CH), 128.7 (CH), 127.5 (CH), 126.9 (CH), 126.7 (CH), 126.2
(CH), 125.2 (CH), 113.8 (C), 33.7 (CH2), 27.0 (CH2), 21.1 (CH2); HRMS
(ES) exact mass calcd for C17H16N3 [MþH]þ: 262.1339, found:
262.1337.
d
171.0 (C), 162.3 (C), 159.8 (C), 151.2 (C), 128.6 (2ꢂ CH), 126.2 (C),
112.0 (C), 111.2 (2ꢂ CH), 39.9 (2ꢂ CH3), 33.7 (CH2), 26.9 (CH2), 21.1
(CH2); HRMS (ES) exact mass calcd for C15H19N4 [MþH]þ: 255.1610,
found: 255.1601.
4.2.15. 2-Quinolin-3-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl-
amine (5p). The title compound was prepared according to gen-
4.2.11. 2-[(4-Cyanophenyl)carbonyl]hexanedinitrile (8). The title
compound was prepared according to general procedure A using
methyl 4-cyanobenzoate (210 mg, 1.30 mmol) and purified by flash
chromatography (0% EtOAc/cyclohexane/100% EtOAc/cyclohex-
ane) to give a colorless oil (38 mg, 12%). IR (film) 2927, 2238 (C^N),
2232 (C^N), 2225 (C^N), 1699, 1406, 1265, 1221, 983, 910,
eral procedure
A
using 3-quinolinecarbonitrile (200 mg,
1.30 mmol) and purified by flash chromatography (0% EtOAc/
cyclohexane/100% EtOAc/cyclohexane/20% MeOH/CH2Cl2) to
give a white solid (105 mg, 31%). Mp 250e252 ꢀC (decomp.); IR
(film) 3395, 3306 (NH), 3180, 2905, 1639, 1581, 1562, 1465, 1428,
1394, 852, 786, 750 cmꢁ1 1H NMR (400 MHz, DMSO-d6)
; d 9.80
852 cmꢁ1
;
1H NMR (400 MHz, CDCl3)
d
8.11e8.08 (2H, m, ArH),
(1H, d, J¼2.0 Hz, ArH), 9.11 (1H, d, J¼1.8 Hz, ArH), 8.13 (1H, d,
J¼7.8 Hz, ArH), 8.06 (1H, d, J¼8.5 Hz, ArH), 7.81e7.77 (1H, m, ArH),
7.66e7.62 (1H, m, ArH), 6.88 (2H, br s, NH2), 2.86 (2H, t, J¼7.7 Hz,
CH2Ar), 2.72 (2H, t, J¼7.4 Hz, CH2Ar), 2.09e2.01 (2H, m,
7.88e7.85 (2H, m, ArH), 4.39 (1H, dd, J¼7.9, 6.0 Hz, CHCN),
2.56e2.45 (2H, m, CH2CN), 2.25e2.12 (2H, m, CH2CH2CH2CN),
2.05e1.88 (2H, m, CH2CH2CN); 13C NMR (100.6 MHz, CDCl3)
d 188.6
(C), 136.5 (C), 133.0 (2ꢂ CH), 129.2 (2ꢂ CH), 118.5 (C), 118.0 (C), 117.3
(C),115.8 (C), 39.1 (CH), 27.6 (CH2), 22.6 (CH2),16.8 (CH2); HRMS (EI)
exact mass calcd for C14H11N3O [M]þ: 237.0897, found: 237.0900.
CH2CH2Ar); 13C NMR (100.6 MHz, DMSO-d6)
d 171.4 (C), 160.2 (C),
149.9 (CH), 148.0 (C), 134.3 (CH), 131.0 (CH), 130.1 (CH), 129.0 (CH),
128.7 (C), 127.3 (CH), 126.9 (C), 114.4 (C), 33.7 (CH2), 27.0 (CH2),
21.1 (CH2); HRMS (ES) exact mass calcd for C16H15N4 [MþH]þ:
263.1297, found: 263.1290.
4.2.12. 2-(3-Fluorophenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-
ylamine (5m). The title compound was prepared according to
general procedure A using 3-fluorobenzonitrile (139
m
L, 1.30 mmol)
4.2.16. 2-Pyridin-4-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl-
amine (5q). The title compound was prepared according to general
procedure A using 4-cyanopyridine (135 mg, 1.30 mmol) and pu-
rified by flash chromatography (0% EtOAc/cyclohexane/100%
EtOAc/cyclohexane/20% MeOH/CH2Cl2) to give a white solid
(60 mg, 22%). Mp 158e160 ꢀC; IR (film) 3324 (NH), 3182, 2957,1681,
and purified by flash chromatography (0% EtOAc/cyclo-
hexane/100% EtOAc/cyclohexane) to give a white solid (285 mg,
96%). Mp 116e118 ꢀC; IR (film) 3311 (NH), 3179, 2957, 2906, 1624,
1571, 1434, 1398, 1381, 851, 773 cmꢁ1 1H NMR (400 MHz, CDCl3)
;
d
8.10e8.09 (1H, m, ArH), 8.03e7.99 (1H, m, ArH), 7.45e7.40 (1H, m,
ArH), 7.17e7.13 (1H, m, ArH), 5.09 (2H, br s, NH2), 2.99 (2H, t,
J¼7.8 Hz, CH2Ar), 2.74 (2H, t, J¼7.4 Hz, CH2Ar), 2.23e2.15 (2H, m,
1630, 1587, 1553, 1456, 1414, 1397, 777 cmꢁ1
CDCl3) 8.69e8.68 (2H, m, ArH), 8.18e8.16 (2H, m, ArH), 5.02 (2H,
br s, NH2), 2.98 (2H, t, J¼7.9 Hz, CH2Ar), 2.74 (2H, t, J¼7.4 Hz, CH2Ar),
2.18e2.15 (2H, m, CH2CH2Ar); 13C NMR (100.6 MHz, CDCl3)
173.3
;
1H NMR (400 MHz,
d
CH2CH2Ar); 13C NMR (100.6 MHz, CDCl3)
d 173.3 (C), 163.0 (C, d,
JF¼244.3 Hz), 162.5 (C, d, JF¼3.1 Hz), 159.3 (C), 140.9 (C, d,
JF¼7.8 Hz), 129.6 (CH, d, JF¼7.9 Hz), 123.5 (CH, d, JF¼2.8 Hz), 116.5
(CH, d, JF¼21.4 Hz), 114.8 (CH, d, JF¼23.0 Hz), 114.4 (C), 34.2 (CH2),
26.7 (CH2), 21.6 (CH2); HRMS (ES) exact mass calcd for C13H13N3F
[MþH]þ: 230.1094, found: 230.1096.
d
(C),161.4 (C), 159.5 (C),150.0 (2ꢂ CH), 145.8 (C), 122.0 (2ꢂ CH),115.5
(C), 34.1 (CH2), 26.8 (CH2), 21.5 (CH2); HRMS (ES) exact mass calcd
for C12H13N4 [MþH]þ: 213.1140, found: 213.1135.
4.2.17. 2-Furan-2-yl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl-
4.2.13. 2-(3-Methyoxyphenyl)-6,7-dihydro-5H-cyclopentapyrimidin-
amine (5r). The title compound was prepared according to a mod-
4-ylamine (5n). The title compound was prepared according to
ification of general procedure A using 2-furonitrile (114 mL,
general procedure
A
using 3-methoxybenzonitrile (159
m
L,
1.30 mmol) in double (2 mL) the standard amount of p-xylene and
purified by flash chromatography (0% EtOAc/cyclohexane/100%
EtOAc/cyclohexane) to give a white solid (107 mg, 41%). Mp
174e175 ꢀC (decomp.); IR (film) 3491, 3316 (NH), 3185, 2956, 1646,
1.30 mmol) and purified by flash chromatography (0% EtOAc/
cyclohexane/100% EtOAc/cyclohexane) to give a white solid
(270 mg, 86%). Mp 166e168 ꢀC; IR (film) 3429, 3314 (NH), 3175,
2960, 2841, 1648, 1570, 1454, 1432, 1394, 1378, 1235, 1043,
1562, 1459, 1395, 1020, 781, 753 cmꢁ1 1H NMR (400 MHz, CDCl3)
;
775 cmꢁ1
;
1H NMR (400 MHz, CDCl3)
d
7.93e7.89 (2H, m, ArH),
d
7.55e7.53 (1H, m, ArH), 7.18 (1H, d, J¼3.3 Hz, ArH), 6.50e6.49 (1H,
7.37e7.33 (1H, m, ArH), 6.99e6.97 (1H, m, ArH), 4.85 (2H, br s, NH2),
m, ArH), 5.01 (2H, br s, NH2), 2.97 (2H, t, J¼7.8 Hz, CH2Ar), 2.72 (2H,