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[ CAS No. 165807-05-6 ] {[proInfo.proName]}

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Chemical Structure| 165807-05-6
Chemical Structure| 165807-05-6
Structure of 165807-05-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 165807-05-6 ]

CAS No. :165807-05-6 MDL No. :MFCD05864792
Formula : C7H11N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OQINWXZQCAIVNK-UHFFFAOYSA-N
M.W : 169.18 Pubchem ID :4913032
Synonyms :

Calculated chemistry of [ 165807-05-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.43
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.19
TPSA : 70.26 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) : -7.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : -0.47
Log Po/w (WLOGP) : 0.03
Log Po/w (MLOGP) : -0.59
Log Po/w (SILICOS-IT) : 0.14
Consensus Log Po/w : 0.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.76
Solubility : 29.1 mg/ml ; 0.172 mol/l
Class : Very soluble
Log S (Ali) : -0.54
Solubility : 48.9 mg/ml ; 0.289 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.59
Solubility : 4.34 mg/ml ; 0.0256 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 165807-05-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 165807-05-6 ]

* 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 [ 165807-05-6 ]
  • Downstream synthetic route of [ 165807-05-6 ]

[ 165807-05-6 ] Synthesis Path-Upstream   1~8

  • 1
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YieldReaction ConditionsOperation in experiment
7%
Stage #1: With hydrogenchloride In water at 48℃; for 16 h;
Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran; water for 1 h;
Stage #3: With sodium hydroxide In tetrahydrofuran; water at 20℃; for 1 h;
Hydrochloric acid (2M, 207 mL, 414 mmol) was added to 4-(dimethoxymethyl)pyrimidin-2-amine (68) (WO 2007/096764) (14.0 g, 83 mmol) and the mixture heated at 48° C. for 16 hr. The mixture was cooled to RT and was neutralized with solid Na2CO3 which produced a precipitate at pH 7. The suspension was diluted with EtOAc (300 mL) and the solid removed by filtration. The organic layer was separated and the aqueous layer was extracted with 1percent MeOH in THF (4×300 mL). The organics were combined, dried and then evaporated in vacuo. The residue (ca. 4.0 g) was suspended in a mixture of MeOH (100 mL), THF (100 mL) and water (100 mL) and treated with NaBH4 (1.57 g, 41.4 mmol). After stirring for 1 hr a solution of NaOH (1M, 20 mL) was added and the mixture was allowed to stand at RT for 48 hr. The solvents were evaporated to give a yellow solid which was partitioned between water (50 mL) and EtOAc (100 mL). The solid which formed at the interface was removed by filtration and the aq layer was extracted with THF (3×300 mL) then dried and evaporated to give a yellow solid. The material was suspended in THF (100 mL) and MeOH (50 mL) and absorbed onto silica gel (20 g) and subjected to column chromatography (80 g, 15percent MeOH in DCM isocratic elution) to give (2-aminopyrimidin-4-yl)methanol (69) as an off-white solid (720 mg, 7percent): m/z 126 (M+H)+ (ES+).
Reference: [1] Patent: US2016/45512, 2016, A1, . Location in patent: Paragraph 0581; 0582
[2] Patent: WO2015/97123, 2015, A1,
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YieldReaction ConditionsOperation in experiment
7% With hydrogenchloride; sodium tetrahydroborate; NaOH In tetrahydrofuran; methanol; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran Intermediate P: 1-(4-((2-Aminopyrimidin-4-yl)methoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea
Hydrochloric acid (2M, 207 mL, 414 mmol) was added to 4-(dimethoxymethyl)pyrimidin-2-amine (68) (WO 2007/096764) (14.0 g, 83 mmol) and the mixture heated at 48° C. for 16 hr.
The mixture was cooled to RT and was neutralized with solid Na2CO3 which produced a precipitate at pH 7.
The suspension was diluted with EtOAc (300 mL) and the solid removed by filtration.
The organic layer was separated and the aqueous layer was extracted with 1percent MeOH in THF (4*300 mL).
The organics were combined, dried and then evaporated in vacuo.
The residue (ca. 4.0 g) was suspended in a mixture of MeOH (100 mL), THF (100 mL) and water (100 mL) and treated with NaBH4 (1.57 g, 41.4 mmol).
After stirring for 1 hr a solution of NaOH (1M, 20 mL) was added and the mixture was allowed to stand at RT for 48 hr.
The solvents were evaporated to give a yellow solid which was partitioned between water (50 mL) and EtOAc (100 mL).
The solid which formed at the interface was removed by filtration and the aq layer was extracted with THF (3*300 mL) then dried and evaporated to give a yellow solid.
The material was suspended in THF (100 mL) and MeOH (50 mL) and absorbed onto silica gel (20 g) and subjected to column chromatography (80 g, 15percent MeOH in DCM isocratic elution) to give (2-aminopyrimidin-4-yl)methanol (69) as an off-white solid (720 mg, 7percent): m/z 126 (M+H)+ (ES+).
Reference: [1] Patent: US2012/244120, 2012, A1,
  • 3
  • [ 6342-56-9 ]
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  • [ 4637-24-5 ]
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YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 110℃; for 15 h;
Stage #2: With sodium hydroxide In water; N,N-dimethyl-formamide at 110℃; for 36 h;
Pyruvic aldehyde dimethyl acetal (10 g, 84 mmol) and N, N’-dimethyl formamide dimethyl diacetal (10 g, 84 mmol) in DMF (30 ml) were heated in a round bottom flask at 110 °C for 15 h. Guanidine hydrochloride (12 g, 127 mmol) and NaOH (6.7 g, 169 mmol) in water were then added to the reaction mixture. The mixture was refluxed for further 36 h. The reaction mass was then cooled and filtered. The product was recrystallized from hot ethyl acetate to yield white crystalline solid 2 (10 g, 70percent).
36%
Stage #1: at 100℃; for 16 h;
Stage #2: With sodium hydroxide In water at 20℃; for 48 h;
Procedure H: Intermediate 8 (1-8) - 2-Aminopyrimidine-4-carboxaldehyde dimethylacetal.; [0093] A solution of 5.5 mL (41 mmol, 1.0 eq.) of dimethylformamide dimethyl acetal and 5.0 mL (41 mmol, 1.0 eq.) pyruvric aldehyde dimethyl acetal was heated at 100 0C for 16 h. Methanol was removed in vacuo to afford a brown oil. A solution of 1.8 g (45 mmol, 1.1 eq.) of sodium hydroxide in 5 mL of water was added to a solution of 4.3 g (45 mmol, 1.1 eq.) of guanidine HCl in 10 mL of water. The resulting solution was added to the above described oil. The resulting mixture was stirred at room temperature for 48 h. The mixture was filtered to provide 2.5 g (15 <n="38"/>mmol, 36percent) of 2-aminopyrimidine-4-carboxaldehyde dimethyl acetal (1-8).
50% With sodium hydroxide In water a)
2-Aminopyrimidine-4-carboxaldehyde dimethyl acetal
Dimethylformamide dimethyl acetal (55 mL, 0.41 mol), and pyruvic aldehyde dimethyl acetal (50 mL, 0.41 mol) were combined and heated to 100° for 18 h.
Methanol was removed in vacuo to afford an oil.
A solution of NaOH (18 g, 0.45 mol) in H2 O (50 mL) was added to guanidine HCl (43 g, 0.45 mol) in H2 O (100 mL), and the resulting solution was added to the above described oil.
The resulting mixture was stirred at 23° for 48 h.
Filtration afforded 25 g (50percent) of the title compound.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 28, p. 3715 - 3717
[2] Patent: EP1227092, 2002, A2, . Location in patent: Page 25
[3] Patent: EP1229035, 2002, A1, . Location in patent: Page 25
[4] Patent: EP1227091, 2002, A2, . Location in patent: Page 25
[5] Patent: WO2007/104053, 2007, A2, . Location in patent: Page/Page column 36-37
[6] Patent: US5593992, 1997, A,
[7] Patent: US5670527, 1997, A,
  • 4
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Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 15, p. 4310 - 4313[2] Angew. Chem., 2017, vol. 129, p. 4374 - 4377,4
[3] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 22, p. 3111 - 3116
[4] Patent: US2008/85898, 2008, A1, . Location in patent: Page/Page column 17
[5] Patent: WO2015/97123, 2015, A1, . Location in patent: Page/Page column 141
  • 5
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YieldReaction ConditionsOperation in experiment
50% With sodium hydroxide In water a
2-Aminopyrimidine-4-carboxaldehyde dimethyl acetal
Dimethylformamide dimethyl acetal (55 mL, 0.41 mol), and pyrrhic aldehyde dimethyl acetal (50 mL, 0.41 mol) were combined and heated to 100° for 18 h.
Methanol was removed in vacuo to afford an oil.
A solution of NaOH (18 g, 0.45 mol) in H2 O (50 mL) was added to guanidine HCl(43 g, 0.45 mol) in H2 O (100 mL), and the resulting solution was added to the above described oil.
The resulting mixture was stirred at 23° for 48 h.
Filtration afforded 25 g (50percent) of the title compound.
Reference: [1] Patent: US5593991, 1997, A,
  • 6
  • [ 165807-06-7 ]
  • [ 165807-05-6 ]
Reference: [1] Patent: EP1229035, 2002, A1, . Location in patent: Page 25
[2] Patent: EP1227091, 2002, A2, . Location in patent: Page 25
  • 7
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Reference: [1] Patent: US6288062, 2001, B1,
  • 8
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 22, p. 3111 - 3116
[2] Patent: WO2015/97123, 2015, A1,
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