6-Methyl-quinazoline-2,4-diamine synthesis

5synthesis methods

Product Name:6-Methyl-quinazoline-2,4-diamine
CAS Number:1955-61-9
Molecular formula:C9H10N4
Molecular Weight:174.2

593-85-1 Synthesis

593-85-1
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64113-84-4 Synthesis

64113-84-4
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1955-61-9
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Yield: 54%

Reaction Conditions:

in N,N-dimethyl acetamide at 140; for 4 h;Inert atmosphere;

Steps:

2,4-Diamino-6-methylquinazoline (20):
0.500 g of 2-fluoro-5-methylbenzonitrile 41 (3.70 mmol) and 1.00 g (5.60 mmol) of guanidine carbonate were dissolved in 5 ml of abs. N,N-dimethylacetamide and heated to 140 °C for 4 h under argon. After cooling a white solid precipitated. The mixture was stored for 18 h in the refrigerator and the product was separated by filtration. After recrystallization from water 350 mg (54 %) of 20 were obtained as colorless crystals. Mp.: 255 °C (lit.255.5-256.6 °C ^[14]). ¹H-NMR(250 MHz, DMSO-d₆): / ppm = 7.76 (s, 1H, Ar-H),7.37-7.26 (dd,J =8.5 Hz,J =1.8 Hz, 1H, Ar-H),7.14 (br, 2H, NH₂),(d,J =8.5 Hz, 1H, Ar-H),5.84 (s, 2H, NH₂),2.32 (s, 3H, CH₃). ¹³C-NMR(75.4 MHz, DMSO-d₆): / ppm = 162.0, 160.2, 150.6, 133.9, 128.6, 124.1, 122.6, 110.0,20.7. IR: ν = 3426 (s), 3344 (w), 3066 (s), 2796 (w), 2681 (w), 1923 (w), 1734 (w), 1672 (s), 1626 (s), 1576 (s), 1516 (s), 1474 (m), 1455 (m), 1427 (s), 1399 (s), 1329 (m), 1289 (m), 1220 (w), 1172 (m), 1139 (w), 1092 (s), 1038 (m), 1002 (m), 962 (w), 922 (m), 874 (m), 857 (m), 824 (s),797 (m), 720 (m), 684 (m), 654 (m), 590 (m), 570 (s). Anal. calcd.for C₉H₁₀N₄(174.20): C 62.05; N 5.79; 32.16; found: C 61.77; N 5.89; 32.40.

References:

Zeiger, Mirco;Stark, Sebastian;Kalden, Elisabeth;Ackermann, Bettina;Ferner, Jan;Scheffer, Ute;Shoja-Bazargani, Fatemeh;Erdel, Veysel;Schwalbe, Harald;G?bel, Michael W. [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 24,p. 5576 - 5580] Location in patent:supporting information

42872-83-3 Synthesis