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[ CAS No. 1642288-47-8 ] {[proInfo.proName]}

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Chemical Structure| 1642288-47-8
Chemical Structure| 1642288-47-8
Structure of 1642288-47-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1642288-47-8 ]

CAS No. :1642288-47-8 MDL No. :
Formula : C15H19N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 273.33 Pubchem ID :-
Synonyms :
Chemical Name :(S)-3-Isopropyl-6-((1-phenylethyl)amino)pyrimidine-2,4(1H,3H)-dione

Calculated chemistry of [ 1642288-47-8 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.33
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 80.8
TPSA : 66.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.7
Log Po/w (XLOGP3) : 2.1
Log Po/w (WLOGP) : 1.78
Log Po/w (MLOGP) : 1.86
Log Po/w (SILICOS-IT) : 2.45
Consensus Log Po/w : 2.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.04
Solubility : 0.251 mg/ml ; 0.000917 mol/l
Class : Soluble
Log S (Ali) : -3.14
Solubility : 0.2 mg/ml ; 0.000733 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.47
Solubility : 0.00928 mg/ml ; 0.000034 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.9

Safety of [ 1642288-47-8 ]

Signal Word:Danger Class:9
Precautionary Statements:P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501 UN#:3077
Hazard Statements:H302-H319-H332-H372-H400 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1642288-47-8 ]

* 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.

  • Downstream synthetic route of [ 1642288-47-8 ]

[ 1642288-47-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 887581-47-7 ]
  • [ 2627-86-3 ]
  • [ 1642288-47-8 ]
YieldReaction ConditionsOperation in experiment
73% In 1,4-dioxane at 80℃; for 18h; 1; 2 Example-2: Preparation of pure Mavacamten 6-Chloro-3 -isopropyl-pyrimidine-2,4-dione (80 g) and 1 ,4-dioxane (400 mL) were charged into a 2000 mL round bottomed flask. (S)-(-)-cL-methylbenzylamine (154.2 g) was added slowly. The mixture was heated to 80 °C and stirred for 18 hours. TLC showed complete consumption of starting material. The reaction mixture was concentrated under vacuum at 80 °C and then cooled to 25 °C. Water (1600 mL) was then added, the mixture obtained was then stirred for 15 minutes, and extracted with ethyl acetate (2 x 800 mL). The organic layer was separated and washed with iN HC1 (400 mL) and brine (800 mL).The product which precipitated from the organic layer was filtered, washed with ethyl acetate (200 mL) and dried under vacuum at 40 °C. Yield: 85 g (Crop 1), Yield: 73%. Purity: 99.84% by HPLC. PXRD pattern is shown in Figure 1.
69% In 1,4-dioxane at 90℃; 1 Compound 1. (S)-3-isopropyl-6-((1-phenylethyl)amino)pyrimidine-2,4(1H,3H)-dione To a solution of 6-chloro-3-isopropylpyrimidine-2,4(lH,3H)-dione (1.3, 1.0 g, 5.31 mmol) in 1,4-dioxane (20 mL) was added (S)-a-methylbenzylamine (Sigma- Aldrich, 1.43 g, 11.7 mmol, 2.2 equiv). The reaction mixture was stirred at 80 °C for 24 h. After cooling to ambient temperature, the mixture was concentrated under reduced pressure. The residual was taken up in EtOAc (70 mL) and washed with aqueous IN HC1 (2 x 50 mL) and brine (40 mL). The organic layer was dried with anhydrous Na2SC"4 and then concentrated under reduced pressure to half the original volume to yield a precipitate. Hexane (20 mL) was added and the mixture was stirred at room temperature. The resulting solid was collected by filtration, washed with hexane (20 mL), and dried to yield 1.0 g (69%) of the title compound as a white solid. LC/MS: m/z (ES+) 274 (M+H)+. 1H-NMR (400 MHz, de-DMSO): δ 9.77 (s, 1H), 7.32 (m, 4H), 7.24 (m, 1H), 6.50 (d, J= 6.8 Hz, 1H), 4.87 (m, 1H), 4.52 (m, 1H), 4.31 (d, J=6.8 Hz, 1H), 1.37 (m, 3H ), 1.24 (m, 6H). 1H NMR (400 MHz, CD3OD) δ ppm 7.39-7.20 (m, 5H), 5.01 (m, 1H), 4.48 (m, 1H), 1.49 (d, J = 6.7 Hz, 3H), 1.36 (m, 6H).
69% In 1,4-dioxane for 24h; 1 Compound 1. (8)-3-Isopropyl-6-((1-phenylethyl) amino) pyrimidine-2,4(1H,3H)-dione. To a solution of 6-chloro-3-isopropylpyrimidine-2,4( 1H,3H)-dione (1.3,1.0 g, 5.31 mmol) in 1,4-dioxane (20 mL) was added (S)-ct-methylbenzylamine (Sigma-Aldrich, 1.43 g, 11.7 mmol, 2.2 equiv). The reaction mixture was stirred at 80 °C for 24 h.After cooling to ambient temperature, the mixture was concentrated under reduced pressure.The residual was taken up in EtOAc (70 mL) and washed with aqueous iN HC1 (2 x 50 mL)and brine (40 mL). The organic layer was dried with anhydrous Na2SO4 and then concentrated under reduced pressure to half the original volume to yield a precipitate. Hexane (20 mL) was added and the mixture was stirred at room temperature. The resulting solid was collected by filtration, washed with hexane (20 mL), and dried to yield 1.0 g (69%)of the title compound as a white solid. LC/MS: mlz (ES+) 274 (M+H)t ‘H-NMR (400 MHz, d6-DMSO): ö 9.77 (s, 1H), 7.32 (m, 4H), 7.24 (m, 1H), 6.50 (d, J= 6.8 Hz, 1H), 4.87 (m, 1H), 4.52 (m, 1H), 4.31 (d, J=6.8 Hz, 1H), 1.37 (m, 3H), 1.24 (m, 6H). ‘H NMR (400 MHz,CD3OD) ö ppm 7.39-7.20 (m, 5H), 5.01 (m, 1H), 4.48 (m, 1H), 1.49 (d, J = 6.7 Hz, 3H), 1.36 (m, 6H).
53% at 100℃; for 5h; Inert atmosphere; 13.1 Compound 1.4. Synthesis of API (Neat 1-Phenylethan-1-amine). Into a 1000-mL round-bottom flask purged and maintained with an inert atmosphere of argon, was placed 6- chloro-3-(propan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione (40 g, 212.08 mmol, 1.00 equiv) in (1S)-1-phenylethan-1-amine (64.4 g, 531.44 mmol, 2.50 equiv). The resulting solution was stirred for 5 h at 100 °C in an oil bath. The residue was applied onto a silica gel column with dichloromethane/methanol (10/1). The crude product was recrystallized from ether. This resulted in 30.7127 g (53%) of 6-[[(1S)-1-phenylethyl]amino]-3-(propan-2-yl)-1,2,3,4- tetrahydropyrimidine-2,4-dione (compound 1.4) as a light yellow solid. LC-MS (ES,m/z) [M+H]+ 274.10, [2M+H]+ 547.25. 1H NMR (300 MHz, DMSO-d6, ppm): δ 9.78 (s, 1H), 7.31- 7.39 (m, 4H), 7.23-7.29 (m, 1H), 6.50-6.52 (d, J = 6.9 Hz, 1H), 4.85-4.95 (m, 1H), 4.44-4.54 (m, 1H), 4.33 (s, 1H), 1.38-1.40 (d, J = 6.0 Hz, 3H), 1.25-1.28 (m, 6H).

  • 2
  • [ 1642288-47-8 ]
  • [ 1642288-48-9 ]
YieldReaction ConditionsOperation in experiment
7% With Selectfluor In acetic acid at 20℃; for 2h; 2 Example 2. (S)-5-fluoro-3-isopropyl-6-((1-phenylethyl)amino)pyrimidine-2,4(1H,3H)-dione (2). To a solution of 1 (80 mg, 0.293 mmol) in acetic acid (2.0 mL) was added selectfluor (104 mg, 0.293 mmol, 1.0 equiv.). The mixture was stirred at room temperature for 2 h. It was then concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with 0-50% EtOAc in hexanes to give 6 mg (7%) of the title compound as a white solid. LC/MS: m/z (ES+) 292 (M+H)+. 1H NMR (400 MHz, CD3OD): δ ppm 7.36-7.24 (m, 5H), 5.04-4.97 (m, 1H), 4.94-4.88 (m, 1H), 1.54 (d, J = 8.0 Hz, 3H), 1.39 (m, 6H).
  • 3
  • [ 1642288-47-8 ]
  • [ 1642288-49-0 ]
YieldReaction ConditionsOperation in experiment
74% With N-Bromosuccinimide In acetic acid at 20℃; for 1h; 3 Example 3. (S)-5-bromo-3-isopropyl-6-((1-phenylethyl)amino)pyrimidine-2,4(1H,3H)-dione (3). To a solution of 1 (55 mg, 0.201 mmol) in acetic acid (1.0 mL) was added N- bromosuccinamide (35 mg, 0.196 mmol). The mixture was stirred at room temperature for 1 hour. It was then concentrated under reduced pressure. The residue was purified by a silica gel column, eluted with 0-40% EtOAc in hexanes to give 52 mg (74%) of the title compound as a white solid. LC/MS: m/z (ES+) 352, 354 (M+H, bromine pattern)+. 1H-NMR (400 MHz, CDCI3) δ ppm 8.96 (br s, 1H), 7.43-7.28 (m, 5H), 5.28 (d, J = 7.4 Hz, 1H), 5.14 (m, 1H), 4.87 (m, 1H), 1.62 (d, J = 6.7 Hz, 3H), 1.45-1.39 (m, 6H).
  • 4
  • [ 69998-14-7 ]
  • [ 1642288-47-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / 50 °C / Inert atmosphere 2: 1,4-dioxane / 90 °C
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