6-Chloro-4,5-pyrimidinediamine

Light yellow solid

A mixture of 4, 6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 2C. 5, 6-Diamino-4-chloropyrimidine; A mixture of 4, 6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 EXAMPLE 13; 6-r4-(Aminophenylmethyl)piperidin-1-yll-7, 9-dihydropurin-8-one; 13A. 5, 6-Diamino-4-chloropyrimidine; A mixture of 4, 6-dichloro-5-aminopyrimidine (Aldrich Chemical Co.) (2.0 g, 12.2 mmol) and concentrated aqueous ammonia (20 ml) was heated to 100 4-Amino- 1 -r8-oxo-8, 9-dihvdro-7H-purin-6-ylVpiperidine-4-carboxylic acid 4- chloro-benzylamide 6A. 5, 6-Diamino-4-chloropyrimidine Step 1: The suspension of 4, 6-dichloropyrimidin-5-amine (1.64 g, 10 mmol) in 5 mL of cone. NHIntermediate 42: 6-Chloro-pyrimidine-4, 5-diamine To a 7 N solution of ammonia in MeOH (40 mL) was added 4, 6-dichloro-pyrimidin-5-ylamine (8.7 g, 53 mmol) and the solution was heated to 100° C. in a sealed tube. After 12 h, the resulting solution was cooled to rt and allowed to stand for 2 h. The colorless crystalline material that resulted was collected by filtration and washed with ice cold MeOH (10 mL) to give the title compound (5.4 g, 71 percent). MS (ESI): mass calcd. for CA suspension of 5-Amino-4, 6-dichloropyrimidine (3 g, 0.02 mol) in ammonia (25 mL, 7N/MeOH, 0.175 mole) was heated at 118° C. overnight (under pressure). The reaction was cooled to 23° C., filtered and washed with ethanol to obtain 1.92 g (70percent).4, [5-DIAMINO-6-HYDROXYPYRIMIDINE] [(1] g) and dimethylaniline [(1] mL) in POC13 (10 [ML)] were heated at reflux under an inert atmosphere for 4 hours. The reaction mixture was concentrated in vacuo, carefully diluted with ice-water and then neutralised with NaHCO3. The product was extracted with EtOAc (4 x 30 mL) and then the organics were dried [(MGS04), ] filtered and concentrated in vacuo. The crude product was triturated with DCM to afford the product as a pale grey solid [(168MG, 15percent)] ; [APOS;H] NMR [(CDC13)] 8 4.95 (br s, 2H), [6. 73] (s, 2H), 7.65 (s, 1H); m/e (MH+MeCN) [+ 186.]Preparation 131 6-Chloro-7, 9-dihydro-purin-8-one Combine 2D. 6-Chloro-7, 9-dihydropurin-8-one; A mixture of the 5, 6-diamino-4-chloropyrimidine of Example 6A (1.0 g, 6.92 mmol) and N, N'-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1, 4-dioxane (20 ml) was refluxed under 13B. 6-Chloro-7, 9-dihydropurin-8-one 6B. 6-Chloro-7, 9-dihydropurin-8-oneA mixture of the 5, 6-diamino-4-chloropyrimidine of Example 6A (1.0 g, 6.92 mmol) and N, N'-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1, 4-dioxane (20 ml) was refluxed under argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86%) LC/MS (LCTl): Rt2.45 [M+H]+ 173, 171.A mixture of the 5, 6-diamino-4-chloropyrimidine of Example 13A (1.0 g, 6.92 mmol) and N, N'-carbonyldiimidazole (2.13 g, 13.2 mmol) in 1, 4-dioxane (20 ml) was refluxed under argon for 48 hours. The solution was concentrated to a brown oil, which was triturated and washed with dichloromethane to give an off-white solid (1.02 g, 86%) LC/MS (LCTl): Rt2.45 [M+H]+ 173, 171.

A chlorinated diaminopyrimidine used in the preparation of various bioactive choloropurine derivatives.

Molecular Weight:144.56
XLogP3:0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:144.0202739
Monoisotopic Mass:144.0202739
Topological Polar Surface Area:77.8
Heavy Atom Count:9
Complexity:98.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes