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[ CAS No. 4316-98-7 ] {[proInfo.proName]}

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Chemical Structure| 4316-98-7
Chemical Structure| 4316-98-7
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Product Details of [ 4316-98-7 ]

CAS No. :4316-98-7 MDL No. :MFCD00023270
Formula : C4H5ClN4 Boiling Point : -
Linear Structure Formula :- InChI Key :VNSFICAUILKARD-UHFFFAOYSA-N
M.W : 144.56 Pubchem ID :78010
Synonyms :

Calculated chemistry of [ 4316-98-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.85
TPSA : 77.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.96
Log Po/w (XLOGP3) : 0.14
Log Po/w (WLOGP) : 0.31
Log Po/w (MLOGP) : -0.63
Log Po/w (SILICOS-IT) : 0.28
Consensus Log Po/w : 0.21

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.32
Solubility : 6.95 mg/ml ; 0.0481 mol/l
Class : Very soluble
Log S (Ali) : -1.33
Solubility : 6.75 mg/ml ; 0.0467 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.53
Solubility : 4.3 mg/ml ; 0.0297 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 4316-98-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4316-98-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 4316-98-7 ]
  • Downstream synthetic route of [ 4316-98-7 ]

[ 4316-98-7 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 4316-98-7 ]
  • [ 13754-19-3 ]
Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 6073,6076
  • 2
  • [ 5413-85-4 ]
  • [ 4316-98-7 ]
YieldReaction ConditionsOperation in experiment
97% With ammonia In water at 100℃; for 46 h; 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 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the EPO <DP n="118"/>product as yellow crystals (1.71 g, 97percent). LC/MS (LCTl): Rt 1.59 [M+H]+ 147, 145.
97% at 100℃; for 46 h; 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 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the product as yellow crystals (1.71 g, 97percent). LC/MS (LCTl): Rt 1.59 [M+H]+ 147, 145.
97% With ammonia In water at 100℃; for 46 h; 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 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the product as yellow crystals (1.71 g, 97percent). LC/MS (LCT1): R, 1.59 [M+H]+ 147, 145.
97% With ammonia In water at 100℃; for 46 h; EXAMPLE 6; 4-Amino- 1 -r8-oxo-8,9-dihvdro-7H-purin-6-ylVpiperidine-4-carboxylic acid 4- chloro-benzylamide 6A. 5,6-Diamino-4-chloropyrimidine <n="94"/>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 0C in a sealed glass tube with vigorous stirring for 18 hours. The cooled tube was recharged with concentrated aqueous ammonia (8 ml), aggregates were broken up, and the mixture was reheated at 100 0C for a further 28 hours. The mixture was evaporated to dryness and the solids were washed with water (20 ml) and dried to give the product as yellow crystals (1.71 g, 97percent). LC/MS (LCTl): Rt 1.59 [MH-H]+ 147, 145.
83% at 100℃; Sealed tube Step 1: The suspension of 4,6-dichloropyrimidin-5-amine (1.64 g, 10 mmol) in 5 mL of cone. NH3 in water in sealed tube was stirred at 100 °C overnight. The solid was collected by filtration and dried under vacuum to give the desired product 6-chloropyrimidine-4,5-diamine as a yellow solid (1.2 g, 83percent yield). LC-MS: m/z 145 (M+H)+.
71% With ammonia In methanol at 100℃; for 12 h; Intermediate 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 C4H5ClN4, 144.0; m/z found, 145.0 [M+H]+. 1H NMR ((CD3)2SO): 7.64 (s, 1H), 6.70. (s, 2H), 4.93 (s, 2H).
70% With ammonia In methanol at 118℃; A 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).

Reference: [1] Patent: WO2006/46023, 2006, A1, . Location in patent: Page/Page column 115-116
[2] Patent: WO2008/75110, 2008, A1, . Location in patent: Page/Page column 116
[3] Patent: WO2007/125315, 2007, A2, . Location in patent: Page/Page column 115
[4] Patent: WO2007/125325, 2007, A1, . Location in patent: Page/Page column 92-93
[5] Organic Process Research and Development, 2011, vol. 15, # 4, p. 841 - 854
[6] Organic Process Research and Development, 2010, vol. 14, # 3, p. 650 - 656
[7] Patent: WO2015/123365, 2015, A1, . Location in patent: Page/Page column 138; 139
[8] Patent: US2009/156599, 2009, A1, . Location in patent: Page/Page column 18
[9] Patent: US2008/51404, 2008, A1, . Location in patent: Page/Page column 114
[10] Journal of the American Chemical Society, 1954, vol. 76, p. 6073,6076
[11] Patent: US5102880, 1992, A,
[12] Patent: US2009/156598, 2009, A1, . Location in patent: Page/Page column 10
[13] European Journal of Medicinal Chemistry, 2010, vol. 45, # 8, p. 3389 - 3393
[14] Patent: US5332744, 1994, A,
  • 3
  • [ 4316-94-3 ]
  • [ 4316-98-7 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 38, p. 7607 - 7611
[2] Journal of the Chemical Society, 1952, p. 4219,4220
[3] Journal of the American Chemical Society, 1953, vol. 75, p. 263,264
[4] Patent: WO2012/37226, 2012, A1, . Location in patent: Page/Page column 124-125
  • 4
  • [ 1672-50-0 ]
  • [ 4316-98-7 ]
YieldReaction ConditionsOperation in experiment
15% for 4 h; Heating / reflux 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.]
Reference: [1] Patent: WO2004/13141, 2004, A1, . Location in patent: Page 134
  • 5
  • [ 33441-77-9 ]
  • [ 4316-98-7 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 10, p. 707 - 712
  • 6
  • [ 4316-98-7 ]
  • [ 530-62-1 ]
  • [ 37527-48-3 ]
YieldReaction ConditionsOperation in experiment
96% for 0.833333 h; Reflux; Inert atmosphere Preparation 131
6-Chloro-7,9-dihydro-purin-8-one
Combine 6-chloro-pyrimidine-4,5-diamine (7.46 mmol; 1.08 g); 1,1'-carbonyldiimidazole (2 equiv; 14.92 mmol; 2.42 g) and 1,4-dioxane (20 mL) and heat to reflux under nitrogen for 50 min.
Evaporate the yellow solution to an oil.
Add DCM (80 mL), let sit 1 h, filter and dry in vacuum oven at 45° C. to provide the title compound (1.22 g; 7.15 mmol; 96percent) MS (ES+): m/z=169 (M-H).
86% for 48 h; Heating / reflux 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 <n="119"/>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, 86percent) LC/MS (LCTl): Rt 2.45 [M+H]+ 173, 171.
86% for 48 h; Heating / reflux 13B. 6-Chloro-7,9-dihydropurin-8-one <n="118"/>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, 86percent) LC/MS (LCT1): Rt 2.45 [M+H]+ 173, 171.
86% for 48 h; Heating / reflux 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, 86percent) LC/MS (LCTl): Rt2.45 [M+H]+ 173, 171.

Reference: [1] Patent: US2010/120801, 2010, A1, . Location in patent: Page/Page column 22
[2] Patent: WO2008/75110, 2008, A1, . Location in patent: Page/Page column 116-117
[3] Patent: WO2007/125315, 2007, A2, . Location in patent: Page/Page column 115-116
[4] Patent: WO2007/125325, 2007, A1, . Location in patent: Page/Page column 93
[5] Patent: WO2006/46023, 2006, A1, . Location in patent: Page/Page column 116
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  • [ 4316-98-7 ]
  • [ 74124-79-1 ]
  • [ 37527-48-3 ]
YieldReaction ConditionsOperation in experiment
78% for 16 h; Heating / reflux Synthesis 20-1 -A; 6-Chloro-7H-purin-8(9H)-one; NXrNH2 A mixture of 4-chloropyrimidine-2,3-diamine (36 mg, 0.25 mmol) and di(/V-succinimidyl)carbonate (128 mg, 0.50 mmol) in acetonitrile (10 mL) was refluxed for 16 hours. The solids formed were collected, washed with acetonitrile (2 x 5 mL) and dried, to give the title compound as a light yellow powder (33 mg, 78percent).1H NMR (500 MHz, de-DMSO) δ 8.35 (1 H, s), 11.90 (2H, s, broad); LC-MS (2) R1 1.96 min; m/z (ESI) 171 [MH+].
Reference: [1] Patent: WO2008/75007, 2008, A1, . Location in patent: Page/Page column 113
  • 8
  • [ 1445-45-0 ]
  • [ 4316-98-7 ]
  • [ 92001-52-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 13, p. 3315 - 3329
  • 9
  • [ 4316-98-7 ]
  • [ 108-24-7 ]
  • [ 92001-52-0 ]
YieldReaction ConditionsOperation in experiment
52% at 120℃; Step 2: A solution of 6-chloropyrimidine-4,5 -diamine (432 mg, 3.0 mmol) in acetic anhydride (5 mL) was heated to 120 °C for overnight. The reaction mixture was concentrated and water was added, and then extracted with EtOAc. The organic layer was separated and washed with water and brine, dried over Na2S04 and concentrated. The residue was suspended in POCI3 (10 mL) and heated to 120 °C for overnight. The reaction was concentrated and diluted with EtOAc and sat. NaHC03 solution. The organic layer was separated and washed with water and brine, dried over Na2S04 and concentrated. Purified by a flash column chromatography (0-30percent EtOAc in petroleum ether) to give the desired product 6-chloro-8-methyl-9H-purine (263 mg, 52percent yield). LC-MS: m/z 169 (M+H)+.
Reference: [1] Patent: WO2015/123365, 2015, A1, . Location in patent: Page/Page column 139
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