Home Cart 0 Sign in  
X

[ CAS No. 2164-67-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 2164-67-2
Chemical Structure| 2164-67-2
Chemical Structure| 2164-67-2
Structure of 2164-67-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 2164-67-2 ]

Related Doc. of [ 2164-67-2 ]

Alternatived Products of [ 2164-67-2 ]

Product Details of [ 2164-67-2 ]

CAS No. :2164-67-2 MDL No. :MFCD01689391
Formula : C5H7N3O Boiling Point : -
Linear Structure Formula :- InChI Key :TWYCDZQLLFNFGK-UHFFFAOYSA-N
M.W : 125.13 Pubchem ID :200493
Synonyms :

Calculated chemistry of [ 2164-67-2 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 32.56
TPSA : 72.03 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) : -7.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.82
Log Po/w (XLOGP3) : -1.0
Log Po/w (WLOGP) : -0.59
Log Po/w (MLOGP) : -1.16
Log Po/w (SILICOS-IT) : 0.06
Consensus Log Po/w : -0.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.41
Solubility : 48.3 mg/ml ; 0.386 mol/l
Class : Very soluble
Log S (Ali) : -0.03
Solubility : 118.0 mg/ml ; 0.942 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.08
Solubility : 10.4 mg/ml ; 0.0832 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 2164-67-2 ]

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

Application In Synthesis of [ 2164-67-2 ]

* 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 [ 2164-67-2 ]
  • Downstream synthetic route of [ 2164-67-2 ]

[ 2164-67-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 2164-66-1 ]
  • [ 2164-67-2 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With sodium tetrahydroborate In ethanol; dichloromethane for 24 h;
Stage #2: With hydrogenchloride In ethannol; dichloromethane; water; acetone at 0℃;
Stage #3: With sodium hydrogencarbonate In ethanol; dichloromethane; water; acetone
2-Amino-4-methoxycarbonylpyrimidine (3.0g, 20mmol, Reference Compound No.3-1) was suspended in a mixture solvent of ethanol (150mL) and dichloromethane (20mL), then sodium borohydride (2.2g, 59mmol) was added thereto at room temperature, and the whole was stirred for 24 hours.
Acetone (20mL) was added gradually under ice-cooling, and then 2M hydrochloric acid was added until the bubbles were no longer formed.
Saturated aqueous sodium hydrogencarbonate solution was added to adjust the pH of the reaction mixture to 8, and the precipitated solid was filtered out.
The filtrate was concentrated under reduced pressure, then suspended in a 10percent methanol-chloroform solution, and the mixture was filtered again with silica gel (5.0g).
The filtrate was evaporated under reduced pressure, the precipitated solid was filterd off with ethyl acetate, and dried under reduced pressure to give 1.8g of the title Reference Compound as a pale yellow solid
(Yield: 73percent)
1H-NMR (400MHz, DMSO-d6)
δ 4.30(s,2H),5.35(s,1H),6.48(s,2H),6.65(d,J = 4.9 Hz,1H),8.19(d,J = 4.9 Hz,1H)
Reference: [1] Patent: EP1864977, 2007, A1, . Location in patent: Page/Page column 17
  • 2
  • [ 165807-05-6 ]
  • [ 2164-67-2 ]
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,
  • 3
  • [ 165807-05-6 ]
  • [ 1220627-33-7 ]
  • [ 2164-67-2 ]
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,
  • 4
  • [ 165807-06-7 ]
  • [ 2164-67-2 ]
Reference: [1] Patent: WO2015/97123, 2015, A1, . Location in patent: Page/Page column 141
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 2164-67-2 ]

Alcohols

Chemical Structure| 33581-98-5

[ 33581-98-5 ]

4-(Hydroxymethyl)pyrimidine

Similarity: 0.86

Chemical Structure| 74502-82-2

[ 74502-82-2 ]

(6-Methylpyrimidin-4-yl)methanol

Similarity: 0.73

Chemical Structure| 143489-45-6

[ 143489-45-6 ]

2-Aminopyrimidin-5-ol

Similarity: 0.71

Chemical Structure| 5734-66-7

[ 5734-66-7 ]

2-Amino-6-ethylpyrimidin-4-ol

Similarity: 0.69

Chemical Structure| 120747-85-5

[ 120747-85-5 ]

2-Aminopyrimidine-5-methanol

Similarity: 0.67

Amines

Chemical Structure| 108-52-1

[ 108-52-1 ]

4-Methylpyrimidin-2-amine

Similarity: 0.84

Chemical Structure| 2164-65-0

[ 2164-65-0 ]

2-Aminopyrimidine-4-carboxylic acid

Similarity: 0.81

Chemical Structure| 165807-05-6

[ 165807-05-6 ]

4-Dimethoxymethylpyrimidin-2-ylamine

Similarity: 0.80

Chemical Structure| 1193-74-4

[ 1193-74-4 ]

4,5-Dimethylpyrimidin-2-amine

Similarity: 0.77

Chemical Structure| 514854-12-7

[ 514854-12-7 ]

6-Ethylpyrimidine-2,4-diamine

Similarity: 0.74

Related Parent Nucleus of
[ 2164-67-2 ]

Pyrimidines

Chemical Structure| 33581-98-5

[ 33581-98-5 ]

4-(Hydroxymethyl)pyrimidine

Similarity: 0.86

Chemical Structure| 108-52-1

[ 108-52-1 ]

4-Methylpyrimidin-2-amine

Similarity: 0.84

Chemical Structure| 2164-65-0

[ 2164-65-0 ]

2-Aminopyrimidine-4-carboxylic acid

Similarity: 0.81

Chemical Structure| 165807-05-6

[ 165807-05-6 ]

4-Dimethoxymethylpyrimidin-2-ylamine

Similarity: 0.80

Chemical Structure| 1193-74-4

[ 1193-74-4 ]

4,5-Dimethylpyrimidin-2-amine

Similarity: 0.77