[ CAS No. 883231-23-0 ] {[proInfo.proName]}

Name: 883231-23-0|N-Boc-2-Amino-5-bromopyrimidine|97%
Brand: Ambeed
SKU: A118359
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Quality Control of [ 883231-23-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 883231-23-0 ]

SDS Specification

Alternatived Products of [ 883231-23-0 ]

Product Details of [ 883231-23-0 ]

CAS No. :	883231-23-0	MDL No. :	MFCD13188600
Formula :	C₉H₁₂BrN₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MQQCCIJHZDEZBW-UHFFFAOYSA-N
M.W :	274.11	Pubchem ID :	18549354
Synonyms :

Calculated chemistry of [ 883231-23-0 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.44
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	59.98
TPSA :	64.11 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.49
Log Po/w (XLOGP3) :	1.79
Log Po/w (WLOGP) :	2.4
Log Po/w (MLOGP) :	0.83
Log Po/w (SILICOS-IT) :	1.31
Consensus Log Po/w :	1.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.7
Solubility :	0.548 mg/ml ; 0.002 mol/l
Class :	Soluble
Log S (Ali) :	-2.75
Solubility :	0.482 mg/ml ; 0.00176 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.46
Solubility :	0.0961 mg/ml ; 0.000351 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.26

Safety of [ 883231-23-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 883231-23-0 ]

* 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 [ 883231-23-0 ]
Downstream synthetic route of [ 883231-23-0 ]

[ 883231-23-0 ] Synthesis Path-Upstream 1~2

1
[ 7752-82-1 ]
[ 24424-99-5 ]
[ 883231-23-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: With dmap; triethylamine In N,N-dimethyl-formamide at 60℃; for 5 h; Stage #2: With potassium carbonate In methanol at 60℃; for 1.5 h;	To a solution of 5-bromopyrimidin-2-amine (11, 5.22 g, 30 mmol) in DMF (50 mL) was added DMAP (366 mg, 3 mmol) and triethylamine (6.3 mL, 75 mmol), followed by the addition of di-tert-butyl dicarbonate (17 mL, 75 mmol). The reaction mixture was stirred at 60 °C for 5 h, then the organic solvent was removed by rotary evaporation. MeOH (50 mL) and K₂CO₃ (2 equiv.) was added to the residue, then the mixture was stirred at 60 °C for 1.5 h. The organic solvent was evaporated, and cold water was added. The formed precipitate was filtered off, washed with water, and dried to provide off-white solid 12 (7.38 g, 90percent yield, R_f = 0.90 in CH₂Cl₂). ¹H NMR (400 MHz, DMSO-d₆) δ: 10.21 (s, 1H), 8.71 (s, 2H), 1.44 (s, 9H). ¹³C NMR (100 MHz, DMSO-d₆) δ: 158.4, 156.5, 150.6, 112.3, 79.7, 27.9. MS (ESI + APCI) m/z: 274.0 [M-H]^-, 276.0 [M+H]⁺.

Reference： [1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 644 - 654

2
[ 209959-33-1 ]
[ 883231-23-0 ]

Reference： [1] Patent: US2014/100366, 2014, A1, . Location in patent: Page/Page column

[ 883231-23-0 ] Synthesis Path-Downstream 1~18

1
[ 209959-33-1 ]
[ 883231-23-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water;	Example 15 tert-Butyl 5-bromopyrimidin-2-ylcarbamate 11 To a solution of <strong>[209959-33-1]2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine</strong> 10 (216 kg crude, 460 mol, assuming quantitative yield in previous step) in anhydrous ethanol (1692 L) was slowly added a solution of sodium hydroxide (55.2 kg, 1380 mol) in water (344 L) while maintaining the temperature at 0-20 C. The mixture was stirred at that temperature until the content of 2-[bis(tert-butoxycarbonyl)-amino]-5-bromopyrimidine (10) was ?0.5% by HPLC. The reaction mixture was cooled to 0-5 C. and the pH was adjusted to 7 by addition of oxalic acid (86.0 kg, 955 mol) while maintaining the temperature below 5 C. The mixture was then distilled under vacuum to a volume of 500-600 L while controlling the temperature below 50 C. Water (800 kg) was added and the mixture was stirred for 1 h. The solid was collected by filtration and stirred with water (2*500 L). The resulting solid was collected by filtration and dried under reduced pressure at 50 C. to afford tert-butyl 5-bromopyrimidin-2-ylcarbamate 11 (107 kg, 85% yield over two steps). 1H NMR (500 MHz, CDCl3) delta 8.63 (s, 2H), 8.12 (s, 1H), 1.55 (s, 9H). LCMS (ESI) m/z [M+H-Boc] 176

Reference： [1]Patent: US2014/100366,2014,A1 .Location in patent: Page/Page column

2
[ 883231-23-0 ]
tert-butyl (5-(4-morpholino-8-nitroquinazolin-2-yl)pyrimidin-2-yl)carbamate [ No CAS ]