Home Cart 0 Sign in  

[ CAS No. 38353-09-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 38353-09-2
Chemical Structure| 38353-09-2
Structure of 38353-09-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 38353-09-2 ]

Related Doc. of [ 38353-09-2 ]

Alternatived Products of [ 38353-09-2 ]

Product Details of [ 38353-09-2 ]

CAS No. :38353-09-2 MDL No. :MFCD00012781
Formula : C4H5ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :IAJINJSFYTZPEJ-UHFFFAOYSA-N
M.W : 132.55 Pubchem ID :122774
Synonyms :

Calculated chemistry of [ 38353-09-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.02
TPSA : 46.01 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) : -7.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.67
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : -0.31
Log Po/w (SILICOS-IT) : 0.62
Consensus Log Po/w : 0.12

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.79
Solubility : 21.3 mg/ml ; 0.16 mol/l
Class : Very soluble
Log S (Ali) : 0.18
Solubility : 200.0 mg/ml ; 1.51 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.99
Solubility : 13.5 mg/ml ; 0.102 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 38353-09-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P313+P332 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 38353-09-2 ]

* 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 [ 38353-09-2 ]
  • Downstream synthetic route of [ 38353-09-2 ]

[ 38353-09-2 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 38353-09-2 ]
  • [ 22536-67-0 ]
Reference: [1] Journal of Physical Chemistry, 1996, vol. 100, # 30, p. 12280 - 12287
  • 2
  • [ 38353-09-2 ]
  • [ 3264-10-6 ]
YieldReaction ConditionsOperation in experiment
39%
Stage #1: at 95℃; for 72 h;
Stage #2: With sodium hydrogencarbonate In ethanol
2-Hydroxypyrimidine HCl (25.92g, 0.20mol) was added in portions to concentrated sulphuric acid (20OmL), then potassium nitrate (39.1 Ig, 0.40mol) was added to the resulting solution and the mixture was stirred for 3 days at 95°C. The mixture was poured slowly into Et2O (3L) with vigorous stirring, the Et2O was repeatedly decanted and then replaced until a solid was obtained. The solid was isolated by filtration, washed with Et2O and was taken up in EtOH. Solid NaHCO3 was added and the mixture was filtered once more. The filtrate was concentrated at reduced pressure to obtain the product (10.72g, 39percent). 1H NMR (CDCl3) 12.00-10.00 (IH, br s), 9.15 (2H, s).
Reference: [1] Patent: WO2007/135350, 2007, A1, . Location in patent: Page/Page column 78
[2] Patent: US2003/181465, 2003, A1,
  • 3
  • [ 38353-09-2 ]
  • [ 32779-37-6 ]
YieldReaction ConditionsOperation in experiment
60% With bromine; sodium hydroxide In water at 20℃; [00159] Scheme 1. Preparation of relevant pyri(mi)dyl halides A-H. Key: (a) NBS, NH4OAc, MeCN, rt, 5 min, pyr: 85-90percent; pym: quant; (b) pyr: RCHO, Na(CN)BH3, MeCN, reflux, 1-12h (82percent, R = C5Hn); pym: NaH, Rl, THF, rt, overnight (85percent, R = Me); (c) Me3(Bn)NBr, f-BuONO, CH2Br2, rt, overnight, pyr: 77-83percent; pym: 30- 40percent; (d) pym: HI, CH2CI2, 0°C, 80-85percent; (e) i. NaOH, Br2, H20, rt, 50-60percent, ii. POCI3, PhNEt2, reflux, 4h, 75-85percent, iii. HI, CH2CI2, 0°C, 80-85percent; (f) ROH, Na, rt, 1-12 h, quant.; (g) RZnl, CI2Pd(PPh3)2, DMF/THF, rt, overnight, pyr (Br): 72percent (R = C6H13), pym (I) 81 percent, (R = C6H13); (h) alkyne, Cul, CI2Pd(PPh3)2, Et3N, MeCN, rt, 1-12 h, quant. [00161] The pyrimidyl bromides were prepared in a similar manner, beginning with bromination of 2-aminopyrimidine. N-Alkylation could not be achieved by reductive amination (presumably due to the decreased nucleophilicity of the amine) and was instead accomplished using NaH and an appropriate alkyl halide to give (B). Nonaqueous diazotization/halo-dediazoniation was used to prepare 5-bromo-2- halopyrimidines, but in diminished yield relative to the analogous reaction with the 2- aminopyridine (again, presumably due to the decreased nucleophilicity of the amine group). Alternatively, 2-pyrimidinone could serve as a precursor to 5-bromo-2- halopyrimidines (Lutz, F.; Kawasaki, T.; Soai, K. Tetrahedron-Asymmetry 2006, 17, 486.) or as a substrate for alkylation to generate 5-bromo-2-alkoxypyrimidines (D) (Kokatla, H. P.; Lakshman, M. K. Org. Lett. 2010, 12, 4478.) Introduction of an alkyne substituent at the 2-position to give ( proceeded satisfactorily under Sonogoshira conditions, but alkylation using Negishi conditions was unselective. Since reduction of the 2- alkynylpyrimidyl bromide (F) to the corresponding 2-alkyl pyrimidyl bromide (H) was complicated by competing removal of the bromine, we turned to 5-bromo-2- iodopyrimidine as a precursor for the cross coupling reactions and saw a dramatic improvement in selectivity and yields.
Reference: [1] Patent: WO2012/162818, 2012, A1, . Location in patent: Page/Page column 45-46
  • 4
  • [ 38353-09-2 ]
  • [ 79387-69-2 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985, vol. 39, # 8, p. 691 - 696
[2] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983, vol. 37, # 4, p. 345 - 350
[3] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6075 - 6087
[4] Patent: CN107540718, 2018, A, . Location in patent: Paragraph 0053-0059; 0080
  • 5
  • [ 38353-09-2 ]
  • [ 79387-69-2 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; for 16 h; Darkness To a solution of pyrimidin-2-ol hydrochloride (5) (12.306 g, 93 mmol) in methanol (357 ml) was added iodine (27.2 g, 107 mmol). The dark purple mixture was stirred at room temperature until all iodine had dissolved. Pulverized silver(I) sulfate (33.4 g, 107 mmol) was added, in one portion, and the mixture was allowed to stir for 16 h in the dark. The yellow Agl precipitate was filtered and the filter cake washed with methanol. The filtrate was treated dropwise with a 50percent aq. KOH solution until pH 10 forming a heavy white precipitate. The resulting alkaline mixture was neutralized (pH 7) with acetic acid and rotoevaporated to dryness in vacuo. The solid residue was suspended in boiling water (-500 mL) and allowed to boil for 30 minutes. Additional water was added portion wise and the heating was continued until a yellow solution was obtained. The solution was allowed to cool to room temperature and placed in fridge for three days. The resulting suspension was filtered with suction, washed with cold water and dried to give compound 6, 5-iodopyrimidin-2(lH)-one (19.34 g, 87 mmol, 94 percent yield) as a yellow solid. MR (500 MHz, DMSO-d6) δ 8.43 (s, 2H), 12.21 (s, 1H); LRMS (ESI) [M-H]- calculated for C1213C4H3IN20 221.9, found 220.9
Reference: [1] Patent: WO2018/143893, 2018, A1, . Location in patent: Page/Page column 6; 22; 24; 25
  • 6
  • [ 102-52-3 ]
  • [ 57-13-6 ]
  • [ 38353-09-2 ]
Reference: [1] Organic Process Research and Development, 2007, vol. 11, # 2, p. 237 - 240
  • 7
  • [ 38353-09-2 ]
  • [ 183438-24-6 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 33, p. 8251 - 8258
  • 8
  • [ 38353-09-2 ]
  • [ 183438-24-6 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 16, p. 6908 - 6916
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 38353-09-2 ]

Alcohols

Chemical Structure| 51953-13-0

[ 51953-13-0 ]

Pyrimidin-2-ol

Similarity: 0.97

Chemical Structure| 166757-62-6

[ 166757-62-6 ]

2-Hydroxypyrimidine-5-carbaldehyde

Similarity: 0.76

Chemical Structure| 51953-18-5

[ 51953-18-5 ]

Pyrimidin-4-ol

Similarity: 0.67

Chemical Structure| 38324-83-3

[ 38324-83-3 ]

2-Hydroxypyrimidine-5-carboxylic acid

Similarity: 0.63

Chemical Structure| 38675-31-9

[ 38675-31-9 ]

4-Phenylpyrimidin-2-ol

Similarity: 0.63

Related Parent Nucleus of
[ 38353-09-2 ]

Pyrimidines

Chemical Structure| 51953-13-0

[ 51953-13-0 ]

Pyrimidin-2-ol

Similarity: 0.97

Chemical Structure| 166757-62-6

[ 166757-62-6 ]

2-Hydroxypyrimidine-5-carbaldehyde

Similarity: 0.76

Chemical Structure| 56621-89-7

[ 56621-89-7 ]

5-Amino-2-methoxypyrimidine

Similarity: 0.74

Chemical Structure| 14001-60-6

[ 14001-60-6 ]

2-Methoxy-4-methylpyrimidine

Similarity: 0.74

Chemical Structure| 38373-44-3

[ 38373-44-3 ]

5-Chloro-2-methoxypyrimidine

Similarity: 0.71