4,6-Dichloro-2-ethyl-5-pyrimidinamine

Intermediate 6: 4-chloro-2-(cyclobex-1-en-I-yI)pyfldln-3-anhlne To a stirred solution of 2, 4-dichloropyridin-3-amrne (CAS 173772-63-9; 750 mg, 4.60 mmol), potassium carbonate (3.18 g, 23.01 mmol) and (cyclohex-i-en-i-yl)boronie acid (CAS 89490-05-1; 869 mg, 6.go mmol) in dioxane (8 mL) and water (2 mL) was tetrakis(triphenylphosphane) palladium (532 mg, 460 iimol). The reaction mixture was heated under microwave irradiation at 140 C for 30 mm. The reaction mixture was filtered (Celite) and then poured into water and extracted with EtOAc. The combined organics were dried (H-frit) and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-20% EtOAc / petroleum ether) to afford the title compoundIntermediate i: 4-chIoro-6-(cyclohcx-1-en-1-yI)-2-ethylpyrirnidin-5- amine mg, 1.27 mmol) in dioxane (io mL) and water (2.5 mL). The reaction mixture was heated under microwave irradiation at 100 C for 40 mm. The crude product was purified by column chromatography (silica, 0-30% EtOAc / petroleum ether) to afford the title compound.?H NMI{ (400 MHz, DMSO-d6) 6ppm ?.17 (t, J=8 Hz, 3 H) 1.59 - 1.75 (m, 4 H) 2.14 - 2.22 (m, 2 H) 2.27- 2.34 (m, 2 H) 2.61 - 2.70 (m, 2 H) 5.14 (s, 2 H) 6.14 (br. s., I H) MS ESi 238EXAMPLE 127 EXAMPLE 128 6-Chloro-5, 6-diamino-2-ethylpyrimidine The material prepared in the foregoing Example 127 (6.19 g, 32 mmol) was dissolved in 2-propanol (75 ml) and 10 ml of anhydrous ammonia was added. This was sealed in a pressure vessel and heated at 110 for 4 hr. The mixture was vented and then evaporated to a solid residue under a stream of nitrogen. This residue was leached with CH2 Cl2 (3*10 ml) and the soluble material (3 g) was shown (tlc, EtOAc:hexanes, 1:1) to be predominantly unreacted starting material, whereas the insoluble material (3.29 g, 19 mmol) was chromatographically pure title compound, suitable for the next reaction (Yield, 60%; quantitative, based on recovered starting material).

Molecular Weight:192.04
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:191.0017026
Monoisotopic Mass:191.0017026
Topological Polar Surface Area:51.8
Heavy Atom Count:11
Complexity:121
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes