[ CAS No. 886366-20-7 ]

Name: 886366-20-7|5-Bromo-N-cyclopropylpyrimidin-2-amine|98%
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Product Details of [ 886366-20-7 ]

CAS No. :	886366-20-7	MDL No. :	MFCD03646032
Formula :	C₇H₈BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	214.06 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 886366-20-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 886366-20-7 ]

Downstream synthetic route of [ 886366-20-7 ]

[ 886366-20-7 ] Synthesis Path-Downstream 1~20

Yield	Reaction Conditions	Operation in experiment
96%
	With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 3h;	Synthesis of (5-bromo-pyrimidin-2-yl)-tert-butyl-amine General procedure: Synthesis of (5-bromo-pyrimidin-2-yl)-tert-butyl-amine To a vial is added R-12 (200 mg, 1.13 mmol) in DMF (5 ml), followed by the addition of K2CO3 (312 mg, 2.26 mmol) and isopropylamine (134 mg, 2.27 mmol). The reaction mixture is stirred at 70° C. for 3 hours. The reaction mixture is concentrated in vacuo. The residue is dissolved in EtOAc, washed with water, brine, dried under anhy. Na2SO4, filtered and concentrated to afford the title intermediate (221 mg); m/z 216.0/218.0 [M/M+2H].

2
[ 32779-36-5 ]
[ 765-30-0 ]
[ 886366-20-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	In tetrahydrofuran at 65℃; for 5h; Sealed tube;
95%	With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 80℃; for 19h; microwave reaction;	64.1 To a 20 mL microwave reaction vial were added 5-bromo-2- chloropyrimidine (500 mg, 2.59 mmol), z-PrOH (7 mL), DIEA (0.90 mL, 5.45 mmol), and cyclopropylamine (0.20 mL, 2.85 mmol). The vial was sealed and heated to 80°C for 19 h, then the mixture was cooled, Celite was added and the mixture was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography, eluting with 0-100% EtOAc in hexanes, to afford (5- bromopyrimidin-2-yl)cyclopropylamine (522.2 mg, 95%) as a solid. LC-MS (ESI) w/z 214, 216 (M +H)+.
95%	In ethanol at 80℃; for 3h;	1.4 Step 4. 5-bromo-N-cyclopropylpyrimidin-2-amine In a pressure tube with one end sealed, add 193 mg 5-bromo-2-chloropyrimidine (1.0 mmol) and 285 mg cyclopropylamine (5.0 mmol) in 3.0 mL ethanol, and the mixture is heated to 80 °Cand stirred for 3 h. The reaction mixture was cooled to room temperature, and 203 mg solid product was collected by filitration for direct useyield: 95%).MS (ESI), m/z: 215 (M+ + H+).

95%	In ethanol at 80℃; for 3h; Sealed tube;	1.4 Step 4. 5-bromo-N-cyclopropylpyrimidin-2-amine In a pressure tube with one end sealed, add 193 mg 5-bromo-2-chloropyrimidine (1.0 mmol) and 285 mg cyclopropylamine (5.0 mmol) in 3.0 mL ethanol, and the mixture is heated to 80° C. and stirred for 3 h. The reaction mixture was cooled to room temperature, and 203 mg solid product was collected by filtration for direct use yield: 95%). MS (ESI), m/z: 215 (M++H+).
95.5%	In tetrahydrofuran at 56℃; for 5h; Sealed tube;	5.1 Step 1. Step 1. 5-Bromo-N-cyclopropylpyrimidin-2-amine A solution of 5-bromo-2-chloropyrimidine (3.87 g, 20 mmol) and cyclopropylamine (5.7 g, 0.1 mol) in 20 mL THF was heated at 65° C. for 5 hrs in a sealed tube. The mixture was evaporated in vacuo, to the residue ethanol was added, after filtration, the cake was washed with ethanol to give 4.07 g product as a colorless solid (95.5%). 1H NMR (300 MHz, CDCl3) δ: 8.32 (2H, s), 5.58 (1H, brs), 2.72 (1H, brs), 0.82-0.84 (2H, m), 0.54 (2H, brs). LCMS: m/z [M+H]+ 214.0011.
86%	In ethanol at 20 - 80℃;	322.3 Step 3: 5-bromo-N-cyclopropyl-pyrimidin-2-amine To a solution of 5-bromo-2-chloro-pyrimidine (2 g, 10.3 mmol) in ethanol (20 mL) at room temperature was added cyclopropylamine (1.18 g, 20.7 mmol). The resulting mixture was stirred at 80° C. overnight. The reaction mixture was diluted with EtOAc and washed with a saturated NaHCO3 aqueous solution. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the title compound (1.9 g, 86% yield) as a white solid. LCMS (M+H)+ 214.
	In ethanol at 80℃; Sealed tube;
1.3 g	With N-ethyl-N,N-diisopropylamine In isopropyl alcohol	5.1 Step 1:5-bromo-N-cyclopropyl-pyrimidin-2-amine synthesis The 1.0g5-bromo -2 chloro pyrimidine dissolved in 15 ml isopropanol, then the 0.35g and cyclopropylamine 1.34gN, N-diisopropyl ethylamine is added to solution in, N 2 protection, heating reflow, precipitating a large amount of white solid. turns on lathe does the solvent, extraction, anhydrous sodium sulfate for drying, filtering, turns on lathe does 1.5g white solid, recrystallization ethyl acetate, to obtain 1.3g white needle-like solid.

Reference： [1]Zhang, Dongfeng; Li, Peng; Gao, Yongxin; Song, Yaoyao; Zhu, Yaqin; Su, Hong; Yang, Beibei; Li, Li; Li, Gang; Gong, Ningbo; Lu, Yang; Shao, Huanjie; Yu, Chunrong; Huang, Haihong [Journal of Medicinal Chemistry, 2021, vol. 64, # 11, p. 7434 - 7452]
[2]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - WO2011/22473, 2011, A1 Location in patent: Page/Page column 167-168
[3]Current Patent Assignee: GUANGZHOU HEALTHQUEST PHARMA - EP2594567, 2013, A1 Location in patent: Paragraph 0054; 0055
[4]Current Patent Assignee: GUANGZHOU HEALTHQUEST PHARMA - US2013/196985, 2013, A1 Location in patent: Paragraph 0125; 0135-0137
[5]Current Patent Assignee: ASTAR BIOTECH - US2014/31354, 2014, A1 Location in patent: Paragraph 0287; 0327; 0328
[6]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2018/296543, 2018, A1 Location in patent: Paragraph 0706; 0710; 0711
[7]Li, Yupeng; Shen, Mengjie; Zhang, Zhang; Luo, Jinfeng; Pan, Xiaofen; Lu, Xiaoyun; Long, Huoyou; Wen, Donghai; Zhang, Fengxiang; Leng, Fang; Li, Yingjun; Tu, Zhengchao; Ren, Xiaomei; Ding, Ke [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10033 - 10046]
[8]Current Patent Assignee: SUN, SHUPING - CN103370324, 2016, B Location in patent: Paragraph 0167-0169

3
[ 886366-20-7 ]
[ 1314640-57-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 80 °C 2: methanol; potassium carbonate / tetrahydrofuran
	Multi-step reaction with 2 steps 1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 24 h / 20 - 100 °C / Inert atmosphere; Sealed tube 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: dichloromethane / 1 h / 20 °C

	Multi-step reaction with 2 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 70 °C / Inert atmosphere 2: potassium carbonate / methanol / 2 h / 60 °C
	Multi-step reaction with 2 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C

Reference： [1]Thomas, Mathew; Huang, Wei-Sheng; Wen, David; Zhu, Xiaotian; Wang, Yihan; Metcalf, Chester A.; Liu, Shuangying; Chen, Ingrid; Romero, Jan; Zou, Dong; Sundaramoorthi, Raji; Li, Feng; Qi, Jiwei; Cai, Lisi; Zhou, Tianjun; Commodore, Lois; Xu, Qihong; Keats, Jeff; Wang, Frank; Wardwell, Scott; Ning, Yaoyu; Snodgrass, Joseph T.; Broudy, Marc I.; Russian, Karin; Iuliucci, John; Rivera, Victor M.; Sawyer, Tomi K.; Dalgarno, David C.; Clackson, Tim; Shakespeare, William C. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3743 - 3748]
[2]Li, Yupeng; Shen, Mengjie; Zhang, Zhang; Luo, Jinfeng; Pan, Xiaofen; Lu, Xiaoyun; Long, Huoyou; Wen, Donghai; Zhang, Fengxiang; Leng, Fang; Li, Yingjun; Tu, Zhengchao; Ren, Xiaomei; Ding, Ke [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10033 - 10046]
[3]Current Patent Assignee: ASTAR BIOTECH - US2014/31354, 2014, A1
[4]Current Patent Assignee: SUN, SHUPING - CN103370324, 2016, B
[5]Zhang, Dongfeng; Li, Peng; Gao, Yongxin; Song, Yaoyao; Zhu, Yaqin; Su, Hong; Yang, Beibei; Li, Li; Li, Gang; Gong, Ningbo; Lu, Yang; Shao, Huanjie; Yu, Chunrong; Huang, Haihong [Journal of Medicinal Chemistry, 2021, vol. 64, # 11, p. 7434 - 7452]

4
[ 886366-20-7 ]
[ 1257628-62-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 80 °C 2: methanol; potassium carbonate / tetrahydrofuran 3: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 80 °C

5
[ 886366-20-7 ]
[ 1066-54-2 ]
N-cyclopropyl-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In N,N-dimethyl-formamide at 80℃;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20 - 100℃; for 24h; Inert atmosphere; Sealed tube;
1.1 g	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 15h; Inert atmosphere;	5.2 5-Bromo-N-cyclopropylpyrimidin-2-amine (1.06 g, 5 mmol), trimethylsilylacetylene (2.5 g, 25 mmol), Pd(PPh3)4 (289 mg, 0.25 mmol) and CuI (71 mg, 0.375 mmol) were placed in a two neck flask with a rubber plug. The mixture underwent 3 cycles of vacuum and filling with Ar2, a solution of DIPEA (968 mg, 0.45 mmol) and DMF (10 mL) was injected to the flask. The mixture was stirred at 80° C. for 15 hrs, and then was poured into 50 mL water, extracted with EtOAc (30 mL×3), organic layer was washed with brine, dried with Na2SO4, filtered, and the filtrate was evaporated in vacuo. The residue was purified by chromatography on silica gel (PE/EtOAc 82:18 to 64:36) to give 1.1 g N-cyclopropyl-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine. This compound was dissolved in 20 mL CH2Cl2, a solution of TBAF (1.3 g, 5 mmol) in 10 mL CH2Cl2 was added into the above solution. The mixture was stirred at rt for 1 h, evaporated in vacuo. The residue was purified by chromatography on silica gel (PE/EtOAc 82:18 to 64:36) to give 0.55 g product as a pale yellow solid (72.8%). 1H NMR (300 MHz, CDCl3) δ: 8.43 (2H, s), 5.77 (1H, brs), 3.18 (1H, s), 2.76-2.81 (1H, m), 0.82-0.87 (2H, m), 0.54-0.59 (2H, m). LCMS: m/z [M+H]+ 160.0863.

1.1 g	With copper(l) iodide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 2h; Inert atmosphere;	5.2 Steps 2:N-cyclopropyl-5 - ((trimethyl silyl) ethynyl) pyrimidine-2-synthesis of amines The 1.0g5-bromo-N-cyclopropyl-pyrimidin-2-amine used 20mlDMF dissolved, then the 0.92g trimethyl silyl acetylene, 0.164gPd (dppf) 2 Cl 2, 0.09g cuprous iodide and 1.51gN, N-diisopropyl ethylamine is added to the solution, the air, plus N 2 protection, heating to 70 °C react about 2h is finished. Extraction, anhydrous sodium sulfate for drying, filtering, turns on lathe does 1.4g crude product, then purified by silica gel column chromatography, using ethyl acetate: petroleum ether = 1:20 elution, shall be 1.1g title compound.
1.1 g	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 15h; Inert atmosphere;

Reference： [1]Location in patent: scheme or table Thomas, Mathew; Huang, Wei-Sheng; Wen, David; Zhu, Xiaotian; Wang, Yihan; Metcalf, Chester A.; Liu, Shuangying; Chen, Ingrid; Romero, Jan; Zou, Dong; Sundaramoorthi, Raji; Li, Feng; Qi, Jiwei; Cai, Lisi; Zhou, Tianjun; Commodore, Lois; Xu, Qihong; Keats, Jeff; Wang, Frank; Wardwell, Scott; Ning, Yaoyu; Snodgrass, Joseph T.; Broudy, Marc I.; Russian, Karin; Iuliucci, John; Rivera, Victor M.; Sawyer, Tomi K.; Dalgarno, David C.; Clackson, Tim; Shakespeare, William C. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3743 - 3748]
[2]Li, Yupeng; Shen, Mengjie; Zhang, Zhang; Luo, Jinfeng; Pan, Xiaofen; Lu, Xiaoyun; Long, Huoyou; Wen, Donghai; Zhang, Fengxiang; Leng, Fang; Li, Yingjun; Tu, Zhengchao; Ren, Xiaomei; Ding, Ke [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10033 - 10046]
[3]Current Patent Assignee: ASTAR BIOTECH - US2014/31354, 2014, A1 Location in patent: Paragraph 0329; 0330
[4]Current Patent Assignee: SUN, SHUPING - CN103370324, 2016, B Location in patent: Paragraph 0170-0172
[5]Zhang, Dongfeng; Li, Peng; Gao, Yongxin; Song, Yaoyao; Zhu, Yaqin; Su, Hong; Yang, Beibei; Li, Li; Li, Gang; Gong, Ningbo; Lu, Yang; Shao, Huanjie; Yu, Chunrong; Huang, Haihong [Journal of Medicinal Chemistry, 2021, vol. 64, # 11, p. 7434 - 7452]

6
[ 886366-20-7 ]
[ 1407999-90-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 24 h / 20 - 100 °C / Inert atmosphere; Sealed tube 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 90 °C

Reference： [1]Li, Yupeng; Shen, Mengjie; Zhang, Zhang; Luo, Jinfeng; Pan, Xiaofen; Lu, Xiaoyun; Long, Huoyou; Wen, Donghai; Zhang, Fengxiang; Leng, Fang; Li, Yingjun; Tu, Zhengchao; Ren, Xiaomei; Ding, Ke [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10033 - 10046]

7
[ 886366-20-7 ]
[ 1257628-83-3 ]
[ 1257628-56-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(l) iodide; palladium diacetate; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere;	1.5 Step 5. 3-(2-(2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (D747) In a pressure tube with one end sealed, add 192 mg step 3 product, 3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl) phenyl)benzamide (0.5 mmol), 107 mg Step 4 product, 5-bromo-N-cyclopropylpyrimidin-2-amine (0.5 mmol), 19 mg CuI (0.1 mmol), 2.2 mg Pd(OAc)2 (0.01 mmol), 2.8 mg PCy3(0.01 mmol) 3.0 mL DMF, 193 mg DIPEA (1.5 mmol), after nitrogen replacement, the solution is heated to 60 °C for 12 h. After cooling to room temperature, the solid is filtered off by 2 cm silical gel column and washed by ethyl acetate for three times, and the solution was concentrated by vacuum evaporation for 193 mg desired product (75%).; 1HNMR (400 MHz, d-DMSO), δ ppm 10.69 (s, 1H), 8.54 (br, 2H), 8.29 (s, 1H), 8.21 (s, 1H), 8.16 (m, 2 H), 7.93 (m, 2H), 7.73 (s, 1H), 7.52 (m, 2H), 2.77 (m, 1H), 2.53 (s, 3H), 2.18 (s, 3H), 0.71 (m, 2H), 0.53 (m, 2H). MS (ESI), m/z: 517 (M++ H+).
75%	With copper(l) iodide; palladium diacetate; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine In N,N-dimethyl-formamide at 60℃; for 12h; Sealed tube; Inert atmosphere;	1.5 Step 5. 3-(2-(2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (D747) In a pressure tube with one end sealed, add 192 mg step 3 product, 3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (0.5 mmol), 107 mg Step 4 product, 5-bromo-N-cyclopropylpyrimidin-2-amine (0.5 mmol), 19 mg CuI (0.1 mmol), 2.2 mg Pd(OAc)2 (0.01 mmol), 2.8 mg PCy3 (0.01 mmol) 3.0 mL DMF, 193 mg DIPEA (1.5 mmol), after nitrogen replacement, the solution is heated to 60° C. for 12 h. After cooling to room temperature, the solid is filtered off by 2 cm silical gel column and washed by ethyl acetate for three times, and the solution was concentrated by vacuum evaporation for 193 mg desired product (75%). 1HNMR (400 MHz, d-DMSO), δ ppm 10.69 (s, 1H), 8.54 (br, 2H), 8.29 (s, 1H), 8.21 (s, 1H), 8.16 (m, 2H), 7.93 (m, 2H), 7.73 (s, 1H), 7.52 (m, 2H), 2.77 (m, 1H), 2.53 (s, 3H), 2.18 (s, 3H), 0.71 (m, 2H), 0.53 (m, 2H). MS (ESI), m/z: 517 (M++H+).
75%	With copper(l) iodide; palladium diacetate; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine In N,N-dimethyl-formamide at 60℃; for 12h; Sealed tube; Inert atmosphere;	3-((2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide General procedure: A mixture of 3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide 8 (192 mg, 0.5 mmol), N-cyclopropyl-5-bromopyrimidin-2-amine9 (107 mg,0.5 mmol), Cu(I)iodide (19mg, 0.1mmol), Pd(OAc)2 (2.2 mg, 0.01 mmol), PCy3 (2.8 mg,0.01 mmol), DIPEA (193 mg, 1.5 mmol), and DMF (3 mL) were added to a sealed tube. The tube was evacuated and backfilled with argon (3 cycles). After stirring at 60°C for 12 h, the reaction mixture was filtered and washed three times with EtOAc. The solvent was removed under vacuum and the resultant crude material was purified by column chromatography to give the title compound 4e (193 mg, yield 75%).1HNMR (400 MHz, d-DMSO), δ ppm 10.69 (s, 1H), 8.54(br, 2H), 8.29 (s, 1H), 8.21 (s, 1H), 8.16 (m, 2 H), 7.93 (m, 2H), 7.73(s, 1H), 7.52 (m, 2H), 2.77 (m, 1H), 2.53 (s, 3H), 2.18 (s, 3H), 0.71 (m, 2H), 0.53(m, 2H). MS (ESI), m/z: 517 (M + H). HRMS (EI): calcd forC28H23F3N6O: 517.1885 [M+H];

Reference： [1]Current Patent Assignee: GUANGZHOU HEALTHQUEST PHARMA - EP2594567, 2013, A1 Location in patent: Paragraph 0056; 0057; 0058
[2]Current Patent Assignee: GUANGZHOU HEALTHQUEST PHARMA - US2013/196985, 2013, A1 Location in patent: Paragraph 0125; 0138-0140
[3]Lu, Xiaoyun; Zhang, Zhang; Ren, Xiaomei; Pan, Xiaofeng; Wang, Deping; Zhuang, Xiaoxi; Luo, Jingfeng; Yu, Rongmin; Ding, Ke [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3458 - 3463]

8
[ 886366-20-7 ]
[ 1581701-29-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / N,N-dimethyl-formamide / 12 h / 100 °C 2: lithium hydroxide; water / tetrahydrofuran; methanol / 3 h / 20 °C 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C

Reference： [1]Cheng, Huimin; Chang, Yu; Zhang, Lianwen; Luo, Jinfeng; Tu, Zhengchao; Lu, Xiaoyun; Zhang, Qingwen; Lu, Jibu; Ren, Xiaomei; Ding, Ke [Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2692 - 2703]

9
[ 886366-20-7 ]
[ 1242458-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / N,N-dimethyl-formamide / 12 h / 100 °C 2: lithium hydroxide; water / tetrahydrofuran; methanol / 3 h / 20 °C

10
[ 67-56-1 ]
[ 201230-82-2 ]
[ 886366-20-7 ]
[ 1581701-22-5 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 12h;

11
[ 886366-20-7 ]
(R)-N-(3 ((2-(cyclopropylamine)pyrimidin-5-yl)ethynyl)-4-methylphenyl)-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-indene-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 70 °C / Inert atmosphere 2: potassium carbonate / methanol / 2 h / 60 °C 3: palladium diacetate; triphenylphosphine; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 80 °C

Reference： [1]Current Patent Assignee: SUN, SHUPING - CN103370324, 2016, B

12
[ 886366-20-7 ]
(S)-N-(3 ((2-(cyclopropylamine)pyrimidin-5-yl)ethynyl)-4-methylphenyl)-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 70 °C / Inert atmosphere 2: potassium carbonate / methanol / 2 h / 60 °C 3: palladium diacetate; triphenylphosphine; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 80 °C

Reference： [1]Current Patent Assignee: SUN, SHUPING - CN103370324, 2016, B

13
[ 886366-20-7 ]
tert-butyl 2-(3-acetyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-1-yl)acetate [ No CAS ]
tert-butyl 2-(3-acetyl-5-(2-(cyclopropylamino)pyrimidin-5-yl)-1H-indazol-1-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 5h;	6.1 Step 1: tert-Butyl 2-(3-acetyl-5-(2-(cyclopropylamino)pyrimidin-5-yl)-1H-indazol-1-yl)acetate (S3) To a solution of 5-bromo-N-cyclopropylpyrimidin-2-amine (S2, 1 equiv) in DMF/H2O (9:1, 10 vol) was added compound S1 (1 equiv), K2CO3(2 equiv), and tetrakis(triphenylphosphine)palladium (0.1 equiv). The reaction mixture was stirred at 90° C. for 5 h and then concentrated under reduced pressure. The remaining residue was purified by column chromatography on silica gel to give compound S3.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2017/35353, 2017, A1 Location in patent: Paragraph 1272

14
[ 886366-20-7 ]
2-chloro-6-[4-[4-[2-(cyclopropylamino)pyrimidin-5-yl]-1-methyl-6-oxo-3-pyridyl]pyrazol-1-yl]benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere; Sealed tube 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; 1,4-dioxane / 2.5 h / 80 °C / Inert atmosphere; Sealed tube

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2018/296543, 2018, A1

15
[ 886366-20-7 ]
[ 73183-34-3 ]
[ 1218789-33-3 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere; Sealed tube;	322.4 Step 4: N-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine A mixture of 5-bromo-N-cyclopropyl-pyrimidin-2-amine (600 mg, 2.8 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.1 g, 4.2 mmol), potassium acetate (550 mg, 5.6 mmol) and PdCl2(PPh3)2(393 mg, 0.56 mmol) in 1,4-dioxane (20 mL) under a nitrogen atmosphere was stirred overnight at 80° C. in a sealed tube. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography to afford the title compound as a yellow solid. LCMS (M+H)+ 180 (M-pinacol).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2018/296543, 2018, A1 Location in patent: Paragraph 0706; 0712; 0713

16
[ 886366-20-7 ]
[ 1542265-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C 3: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

17
[ 886366-20-7 ]
[ 1542265-19-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C 3: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

18
[ 886366-20-7 ]
[ 1542265-46-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C 3: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

19
[ 886366-20-7 ]
3-((2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-N-(3,3-difluoro-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-5-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C 3: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

20
[ 886366-20-7 ]
(S)-3-((2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-N-(3,3-difluoro-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-5-yl)-4-methylbenzamide [ No CAS ]
(R)-3-((2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-N-(3,3-difluoro-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-5-yl)-4-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C 3: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere 4: carbon dioxide; diethylamine / ethanol / Resolution of racemate

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Historical Records

Related Functional Groups of
[ 886366-20-7 ]

Bromides

[ 77476-95-0 ]

(5-Bromopyrimidin-2-yl)isopropylamine

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[ 1187385-92-7 ]

5-Bromo-N-propylpyrimidin-2-amine

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[ 947534-33-0 ]

5-Bromo-N-cyclobutylpyrimidin-2-amine

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[ 14001-71-9 ]

5-Bromo-N-butylpyrimidin-2-amine

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[ 14001-72-0 ]

5-Bromo-N-(tert-butyl)pyrimidin-2-amine

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Amines

[ 77476-95-0 ]

(5-Bromopyrimidin-2-yl)isopropylamine

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[ 1187385-92-7 ]

5-Bromo-N-propylpyrimidin-2-amine

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[ 947534-33-0 ]

5-Bromo-N-cyclobutylpyrimidin-2-amine

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[ 14001-71-9 ]

5-Bromo-N-butylpyrimidin-2-amine

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5-Bromo-N-(tert-butyl)pyrimidin-2-amine

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Related Parent Nucleus of
[ 886366-20-7 ]

Pyrimidines

[ 77476-95-0 ]

(5-Bromopyrimidin-2-yl)isopropylamine

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[ 1187385-92-7 ]

5-Bromo-N-propylpyrimidin-2-amine

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[ 947534-33-0 ]

5-Bromo-N-cyclobutylpyrimidin-2-amine

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5-Bromo-N-butylpyrimidin-2-amine

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5-Bromo-N-(tert-butyl)pyrimidin-2-amine

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P342	If experiencing respiratory symptoms:
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P378
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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H202	Explosive; severe projection hazard
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H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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Health hazards
Code	Phrase
H300	Fatal if swallowed
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H302	Harmful if swallowed
H303	May be harmful if swallowed
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H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
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Code	Phrase
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 886366-20-7 ]

Quality Control of [ 886366-20-7 ]

Related Doc. of [ 886366-20-7 ]

Product Details of [ 886366-20-7 ]

Safety of [ 886366-20-7 ]

Application In Synthesis of [ 886366-20-7 ]

[ 886366-20-7 ] Synthesis Path-Downstream 1~20

Related Functional Groups of [ 886366-20-7 ]

Bromides

Amines

Related Parent Nucleus of [ 886366-20-7 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

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Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 886366-20-7 ]

Related Parent Nucleus of
[ 886366-20-7 ]