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[ CAS No. 70183-89-0 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 70183-89-0
Chemical Structure| 70183-89-0
Structure of 70183-89-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 70183-89-0 ]

CAS No. :70183-89-0 MDL No. :MFCD11506173
Formula : C5H9ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :FZQPHVOBOIVWKP-UHFFFAOYSA-N
M.W : 148.59 Pubchem ID :45792534
Synonyms :

Calculated chemistry of [ 70183-89-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.11
TPSA : 52.05 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) : -6.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.46
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : -0.16
Log Po/w (SILICOS-IT) : 0.86
Consensus Log Po/w : 0.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.4
Solubility : 5.97 mg/ml ; 0.0402 mol/l
Class : Very soluble
Log S (Ali) : -1.12
Solubility : 11.2 mg/ml ; 0.0756 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.61
Solubility : 3.63 mg/ml ; 0.0244 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.26

Safety of [ 70183-89-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 70183-89-0 ]

* 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.

  • Downstream synthetic route of [ 70183-89-0 ]

[ 70183-89-0 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 543712-91-0 ]
  • [ 70183-89-0 ]
  • N-[(3-methylisoxazol-5-yl)methyl]-N'-(5-methyl-2H-pyrazol-3-yl)pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 115℃; for 18.0h; Example 1; N-[(3-methylisoxazol-5-yl)methyl]-N'-(5-methyl-2H-pyrazol-3-yl)pyrimidine-2,4-diamine (also known as N-[(3-methyl-1,2-oxazol-5-yl)methyl]-N'-(5-methyl-2H-pyrazol-3-yl)pyrimidine-2,4-diamine); A mixture of 2-chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (0.209 g, 1.0 mmol), <strong>[70183-89-0](3-methylisoxazol-5-yl)methanamine hydrochloride</strong> (also known as (3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride; 0.446 g, 3.0 mmol) and N,N-diisopropylethylamine (0.693 ml, 4.0 mmol) in n-butanol (10 ml) was heated at 115 C. for 18 hours. The mixture was evaporated under vacuum and the residue was then partitioned between water (20 ml) and diethyl ether (20 ml). The mixture was filtered and the residue washed with water and then allowed to dry to leave compound 1 in table 1 (0.264 g, 93% yield).1H NMR (300 MHz, DMSO): 2.17 (s, 3H), 2.18 (s, 3H), 4.53 (d, 2H), 6.11 (s, 1H), 6.14-6.42 (m, 2H), 7.19 (s, 1H), 7.83 (d, 1H), 9.32 (s, 1H), 11.84 (s, 1H).MS: m/z 286 (MH+).
  • 2
  • 2-chloro-N-[5-[2-(4-methoxyphenyl)ethyl]-1H-pyrazol-3-yl]pyrimidin-4-amine [ No CAS ]
  • [ 70183-89-0 ]
  • N'-[5-[2-(4-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]-N-[(3-methylisoxazol-5-yl)methyl]pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With N-ethyl-N,N-diisopropylamine; In 2-methoxy-ethanol; at 170℃; for 3.0h;Microwave irradiation; Example 24; N'-[5-[2-(4-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]-N-[(3-methylisoxazol-5-yl)methyl]pyrimidine-2,4-diamine (also known as N'-[5-[2-(4-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]-N-[(3-methyl-1,2-oxazol-5-yl)methyl]pyrimidine-2,4-diamine); A mixture of 2-chloro-N-[5-[2-(4-methoxyphenyl)ethyl]-1H-pyrazol-3-yl]pyrimidin-4-amine (0.10 g, 0.3 mmol), <strong>[70183-89-0](3-methylisoxazol-5-yl)methanamine hydrochloride</strong> (also known as (3-methyl-i1,2-oxazol-5-yl)methanamine hydrochloride; 0.068 g, 0.45 mmol) and N,N-diisopropylethylamine (0. 159 ml, 0.91 mmol) in 2-methoxyethanol (3 ml) was heated at 170 C. in a Emrys Optimiser microwave for 3 hours. The mixture was concentrated in vacuo and the residue was dissolved in a mixture of dimethylformamide and acetonitrile (1 :3.8) and purified directly by preparative hplc eluting with a gradient of acetonitrile in water containing 1% ammonia. The fractions containing product were combined and evaporated to leave compound 18 in table 3 (0.039 g, 32% yield).1H NMR (300 MHz, DMSO): 2.16 (3H, s), 2.71-2.88 (4H, m), 3.71 (3H, s), 4.53 (2H, d), 6.10 (1H, s), 6.23 (2H, s), 6.84 (2H, d), 7.14 (2H, d), 7.22 (1H, s), 7.83 (1H, d), 9.40 (1H, s), 11.93 (1H, s).MS: m/z 406 (MH+).
  • 3
  • [ 1000895-37-3 ]
  • [ 70183-89-0 ]
  • N'-[5-[2-(3-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]-N-[(3-methylisoxazol-5-yl)methyl]pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With N-ethyl-N,N-diisopropylamine; In 2-methoxy-ethanol; at 200℃;Microwave irradiation; Example 27; N'-[5-[2-(3-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]-N-[(3-methylisoxazol-5-yl)methyl]pyrimidine-2,4-diamine (also known as N'-[5-[2-(3-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]-N-[(3-methyl-1,2-oxazol-5-yl)methyl]pyrimidine-2,4-diamine); A mixture of 2-chloro-N-[5-[2-(3-methoxyphenyl)ethyl]-1H-pyrazol-3-yl]pyrimidin-4-amine (0.10 g, 0.3 mmol), <strong>[70183-89-0](3-methylisoxazol-5-yl)methanamine hydrochloride</strong> (also known as (3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride; 0.091 g, 0.6 mmol) and N,N-diisopropylethylamine (0.212 ml, 1.2 mmol) in 2-methoxyethanol (3 ml) was heated at 200 C. in a Emrys Optimiser microwave for 2 hours. The mixture was concentrated in vacuo and the residue was dissolved in a mixture of dimethylformamide and acetonitrile (1:3.8) and purified directly by preparative hplc eluting with a gradient of acetonitrile in water containing 1% ammonia. The fractions containing product were combined and concentrated. The resultant precipitate was filtered and the residue was washed with water and then dried under vacuum to leave compound 21 in table 3 (0.041 g, 34% yield).H NMR (300 MHz, DMSO): 2.16 (3H, s), 2.76-2.95 (4H, m), 3.73 (3H, s), 4.53 (2H, d), 6.10 (1H, s), 6.19-6.37 (2H, m), 6.72-6.85 (3H, m), 7.13-7.25 (2H, m), 7.83 (1H, s), 9.34 (1H, s), 11.90 (1H, s).MS: m/z 406 (MH+).
  • 4
  • [ 1000895-39-5 ]
  • [ 70183-89-0 ]
  • N-[(3-methylisoxazol-5-yl)methyl]-N'-(5-phenethyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With N-ethyl-N,N-diisopropylamine; In 2-methoxy-ethanol; at 170℃; for 2.0h;Microwave irradiation; Example 30; N-[(3-methylisoxazol-5-yl)methyl]-N'-(5-phenethyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (also known as N-[(3-methyl-1,2-oxazol-5-yl)methyl]-N'-(5-phenethyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine); A mixture of 2-chloro-N-(5-phenethyl-1H-pyrazol-3-yl)pyrimidin-4-amine (0.10 g, 0.33 mmol), <strong>[70183-89-0](3-methylisoxazol-5-yl)methanamine hydrochloride</strong> (also known as (3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride; 0.06 g, 0.4 mmol) and N,N-diisopropylethylamine (0. 175 ml, 1.0 mmol) in 2-methoxyethanol (2 ml) was heated at 170 C. in a Emrys Optimiser microwave for 2 hours. A further portion of <strong>[70183-89-0](3-methylisoxazol-5-yl)methanamine hydrochloride</strong> (also known as (3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride; 0.015 g, 0.1 mmol) was added and the mixture heated at 200 C. in the microwave for 1 hour. The mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The organic phase was separated and then washed with brine. The organic phase was dried over magnesium sulfate and then evaporated. The residue was dissolved in a mixture of dimethylformamide and acetonitrile (1:3.8) and purified directly by preparative hplc eluting with a gradient of acetonitrile in water (containing 1% ammonia). The fractions containing product were evaporated to leave compound 24 in table 3 (0.051 g, 41% yield).1H NMR (300 MHz, DMSO): 2.17 (3H, s), 2.86 (4H, m), 4.53 (2H, d), 6.11 (1H, s), 6.24 (2H, s), 7.13-7.33 (6H, m), 7.83 (1H, d), 9.37 (1H, s), 11.93 (1H, s).MS: m/z 376 (MH+).
  • 5
  • [ 1000895-84-0 ]
  • [ 70183-89-0 ]
  • N-[(3-methyl-1,2-oxazol-5-yl)methyl]-N'-[5-[2-(3-propan-2-yloxyphenyl)ethyl]-1H-pyrazol-3-yl]pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With N-ethyl-N,N-diisopropylamine; In 2-methoxy-ethanol; at 180℃; for 1.5h;Microwave irradiation; Example 122; N-[(3-methyl-1,2-oxazol-5-yl)methyl]-N'-[5-[2-(3-propan-2-yloxyphenyl)ethyl]-1H-pyrazol-3-yl]pyrimidine-2,4-diamine2-chloro-N-[5-[2-(3-propan-2-yloxyphenyl)ethyl]-1H-pyrazol-3-yl]pyrimidin-4-amine (60 mg, 0. 17 mmol, 1 eq) was dissolved in 2-methoxyethanol (5 ml) and (3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride (50 mg, 0.34 mmol, 2 eq) and N-ethyl-N-propan-2-yl-propan-2-amine (103 μl, 0.59 mmol, 3.5 eq) were added. The mixture was heated to 180 C. for 90 mins in the microwave reactor. The solvent was evaporated under reduced pressure and the residue purified by basic reverse-phase prep HPLC (gradient 25-75% MeCN in 1% aq NH3). Clean fractions were evaporated to afford N-[(3-methyl-1,2-oxazol-5-yl)methyl]-N'-[5-[2-(3-propan-2-yloxyphenyl)ethyl]-1H-pyrazol-3-yl]pyrimidine-2,4-diamine (25.4 mg, 35%) as a beige solid.1H NMR (399.902 MHz, DMSO) δ 1.17 (d, J=6.0 Hz, 6H), 2.10 (s, 3H), 2.78 (m, 4H), 3.21 (s, 1H), 4.48 (m, 3H), 6.03 (s, 1H), 6.21 (s, 1H), 6.68 (m, 3H), 7.10 (m, 2H), 7.75 (d, J=5.8 Hz, 1H), 9.27 (s, 1H), 11.83 (s, 1H). MS: m/z=434 (MH+)
  • 6
  • N-(5-benzyloxy-1H-pyrazol-3-yl)-2-chloro-pyrimidin-4-amine [ No CAS ]
  • [ 70183-89-0 ]
  • N'-(5-benzyloxy-1H-pyrazol-3-yl)-N-[(3-methylisoxazol-5-yl)methyl]pyrimidine-2,4-diamine formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% Example 72; N'-(5-benzyloxy-1H-pyrazol-3-yl)-N-[(3-methylisoxazol-5-yl)methyl]pyrimidine-2,4-diamine (also known as N-[(3-methyl-1,2-oxazol-5-yl)methyl]-N'-(5-phenylmethoxy-1H-pyrazol-3-yl)pyrimidine-2,4-diamine)A mixture of N-(5-benzyloxy-1H-pyrazol-3-yl)-2-chloro-pyrimidin-4-amine (0.045 g, 0.15 mmol), <strong>[70183-89-0](3-methylisoxazol-5-yl)methanamine hydrochloride</strong> (also known as (3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride; 0.045 g, 0.3 mmol) and di-iso-propylethylamine (0.078 ml, 0.45 mmol) in 2-methoxyethanol (2 ml) was heated at 160 C. for 1 hour in an Emrys Optimiser microwave. The mixture was evaporated and the residue purified by preparative hplc eluting with a gradient of acetonitrile in water both containing 1% formic acid to give example 72 in table 4 as the formate salt (0.008 g, 13% yield).MS: m/z 378 (MH+).
  • 7
  • [ 1000896-44-5 ]
  • [ 70183-89-0 ]
  • N4-[5-(2-methoxy-1-methylethoxy)-1H-pyrazol-3-yl]-N2-[(3-methylisoxazol-5-yl)methyl]pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With N-ethyl-N,N-diisopropylamine; In 2-methoxy-ethanol; at 160℃; for 0.833333h;Microwave irradiation; Example 75; N4-[5-(2-methoxy-1-methylethoxy)-1H-pyrazol-3-yl]-N2-[(3-methylisoxazol-5-yl)methyl]pyrimidine-2,4-diamine (also known as N'-[5-(1-methoxypropan-2-yloxy)-1H-pyrazol-3-yl]-N-[(3-methyl-1,2-oxazol-5-yl)methyl]pyrimidine-2,4-diamine)2-Chloro-N-[5-(2-methoxy-1-methylethoxy)-1H-pyrazol-3-yl]pyrimidin-4-amine (55 mg, 0.194 mmol) and [(3-methylisoxazol-5-yl)methyl]amine. HCl (also known as (3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride; 58 mg, 0.388 mmol) were heated with DIPEA (102ul, 0.582 mmol) in 2-methoxyethanol (2 ml) in a microwave reactor at 160 C. for an initial period of 30 min, then for a further 20 min. The solution was evaporated to dryness and the residue was purified by reverse phase acidic prep hplc, using a gradient of 5-50% MeCN in H2O+0.2% TFA. The product fractions were neutralised with aqueous NaHCO3, concentrated under vacuum to remove organic solvents and extracted with ethyl acetate (3×15 ml). The combined extracts were dried over MgSO4, filtered and evaporated. The gummy residue was triturated with a mixture of ether and hexane to crystallize the product, the solvent was evaporated and the product was dried under vacuum to afford the title compound as a white solid (30 mg, 43% yield).1H NMR (300.132 MHz, DMSO) δ 1.24 (d, 3H), 2.19 (s, 3H), 3.30 (s, 3H-obscured by water peak), 3.36-3.54 (m, 2H), 4.58 (d, 2H), 4.62-4.76 (m, 1H), 5.23 (bs, 1H), 6.04 (bs, 1H), 6.16 (s, 1H), 7.67 (bs, 1H), 7.90 (d, 1H), 9.97 (bs, 1H), 11.86 (bs, 1H); MS: m/z 360 (MH+)
  • 8
  • 2-chloro-N-[5-[(3-methoxy-5-methyl-phenyl)methoxy]-2H-pyrazol-3-yl]pyrimidin-4-amine [ No CAS ]
  • [ 70183-89-0 ]
  • N'-[5-[(3-methoxy-5-methyl-phenyl)methoxy]-1H-pyrazol-3-yl]-N-[(3-methyl-1,2-oxazol-5-yl)methyl]pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With N-ethyl-N,N-diisopropylamine; In ethanol; at 180℃; for 0.75h;Microwave irradiation; Example 131; N'-[5-[(3-methoxy-5-methyl-phenyl)methoxy]-1H-pyrazol-3-yl]-N-[(3-methyl-1,2-oxazol-5-yl)methyl]pyrimidine-2,4-diamine2-chloro-N-[5-[(3-methoxy-5-methyl-phenyl)methoxy]-2H-pyrazol-3-yl]pyrimidin-4-amine (73 mg, 0.2 mmol), (3-methyl-1,2-oxazol-5-yl)methanamine. hydrochloride (38 mg, 0.25 mmol) and N-ethyl-N-propan-2-yl-propan-2-amine (112 uL, 0.63 mmol) in ethanol (4 ml) were heated at 180 C. in a microwave reactor for 45 mins. The reaction mixture was cooled and the solution concentrated. The crude product was purified by reverse-phase prep. HPLC (basic) using a 35-55% gradient of acetonitrile in water containing 1% ammonium hydroxide solution. The clean fractions were taken and evaporated to afford the title compound as a gum. (8 mg, 9% yield). H NMR (500.13 MHz, DMSO-d6) δ 2.17 (3H, m), 2.27 (3H, s), 3.72 (3H, s) 4.50-4.59 (2H, m), 5.03, (2H, s), 5.30 (1H, s), 5.99 (1H, s), 6.13 (1H, s), 6.68 (1H, s), 6.75 (1H, s), 6.80 (1H, s), 7.67 (1H, s), 7.89 (1H, d), 10.08 (1H, s), 11.95 (1H, s). MS: m/z 422 (MH+).
  • 9
  • 2-chloro-N-[5-[2-(2-furyl)ethyl]-2H-pyrazol-3-yl]pyrimidin-4-amine [ No CAS ]
  • [ 70183-89-0 ]
  • N'-[5-[2-(2-furyl)ethyl]-2H-pyrazol-3-yl]-N-[(3-methyl-1,2-oxazol-5-yl)methyl]pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With N-ethyl-N,N-diisopropylamine; In 2-methoxy-ethanol; at 190℃; for 4.0h;Microwave irradiation;Product distribution / selectivity; Example 107; N'-[5-[2-(2-furyl)ethyl]-2H-pyrazol-3-yl]-N-[(3-methyl1,2-oxazol-5-yl)methyl]pyrimidine-2,4-diamineA mixture of 2-chloro-N-[5-[2-(2-furyl)ethyl]-2H-pyrazol-3-yl]pyrimidin-4-amine (100 mg, 0.35 mmol, 1 eq), (3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride (62 mg, 0.42 mmol, 1.5 eq) and diisopropylethylamine (159[l, 0.91 mmol, 3 eq) in methoxyethanol (3 ml) was heated in the microwave at 190 C. for 240 mins before evaporating solvent under reduced pressure. The crude product was purified on the acidic reverse phase hplc using a 20-40% gradient of acetonitrile in water containing 0.2% TFA. The clean fractions were taken and loaded onto a SCX-3 column pre-wet with methanol. After washing through three times with methanol the product was finally eluted with 10% ammonia solution in methanol. After evaporation to low volume a white solid was obtained. (68.7 mg, 48% yield)1H NMR (300.132 MHz, DMSO): δ 2.17 (s, 3H), 2.80-2.99 (m, 4H), 4.54 (d, 2H), 6.11 (d, 2H), 6.22-6.33 (m, 2H), 6.34 (dd, 1H), 7.23 (s, 1H), 7.51 (d, 1H), 7.82 (d, 1H), 9.41 (s, 1H), 11.95 (s, 1H). MS: m/z 366 (MH+).
  • 10
  • [ 915720-61-5 ]
  • [ 70183-89-0 ]
  • [ 1000896-32-1 ]
YieldReaction ConditionsOperation in experiment
51% With N-ethyl-N,N-diisopropylamine; In 2-methoxy-ethanol; at 200℃; for 0.5h;Microwave irradiation; b) A mixture of 5-bromo-2-chloro-N-(5-isopropoxy- I H-pyrazol-3-yl)pyrimidin-4-amine (0.20 g, 0.6 mmol), N-[(3-methylisoxazol-5-yl)methyl]methanamine hydrochloride (also known as N-methyl-1-(3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride; 0.116 g, 0.78 mmol) and di-iso-propylethylamine (0.419 ml, 2.4 mmol) in 2-methoxyethanol (3 ml) was heated in a microwave at 200 C. for 30 minutes. The mixture was concentrated and the residue purified by flash chromatography on silica eluting with a mixture of 50% iso-hexane in ethylacetate. The fractions containing product were combined and evaporated to leave 5-bromo-N'-(5-isopropoxy-1H-pyrazol-3-yl)-N-[(3-methylisoxazol-5-yl)methyl]pyrimidine-2,4-diamine (also known as 5-bromo-N-[(3-methyl-1,2-oxazol-5-yl)methyl]-N'-(5-propan-2-yloxy-1H-pyrazol-3-yl)pyrimidine-2,4-diamine) (0. 125 g, 51% yield). MS: m/z 408 (MH+).
  • 11
  • [ 1000896-37-6 ]
  • [ 70183-89-0 ]
  • [ 1000896-36-5 ]
YieldReaction ConditionsOperation in experiment
32% With N-ethyl-N,N-diisopropylamine; In hexan-1-ol; at 120℃; for 3.0h; b) A mixture of 2,6-dichloro-N-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidin-4-amine (0.350 g, 1.21 mmol), <strong>[70183-89-0](3-methylisoxazol-5-yl)methanamine hydrochloride</strong> (also known as (3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride; 0.361 g, 2.43 mmol) and di-iso-propylethylamine (0.634 ml, 3.64 mmol) was heated in 1-hexanol (5 ml) at 120 C. for 3 hours. The mixture was evaporated and the residue was dissolved in ethyl acetate (20 ml) and then washed with water (20 ml) followed by brine (20 ml). The organic extract was dried over magnesium sulfate, filtered and then evaporated to leave a yellow oil. The oil was purified by chromatography on silica eluting with a mixture of 0-5% methanol in dichloromethane. Fractions containing product were combined and evaporated to leave a solid that was triturated with diethyl ether to give 6-chloro-N'-(5-isopropoxy-1H-pyrazol-3-yl)-N-[(3-methylisoxazol-5-yl)methyl]pyrimidine-2,4-diamine (also known as 6-chloro-N-[(3-methyl-1,2-oxazol-5-yl)methyl]-N'-(5-propan-2-yloxy-1H-pyrazol-3-yl)pyrimidine-2,4-diamine; 0.140 g, 32% yield). 1H NMR (500 MHz, DMSO 373K): 1.26 (d, 6H), 2.18 (s, 3H), 4.55 (m, 3H), 5.47 (bs, 1H), 6.1-6.25 (m, 2H), 7.55 (bs, 1H), 9.5 (bs, 1H), 11.45 (bs, 1H). MS: m/z 364 (MH+).
  • 12
  • [ 6328-58-1 ]
  • [ 70183-89-0 ]
  • [ 1000896-34-3 ]
YieldReaction ConditionsOperation in experiment
32% With N-ethyl-N,N-diisopropylamine; In diethylene glycol dimethyl ether; at 160℃; for 3.0h; 4-chloro-6-methyl-N-[(3-methylisoxazol-5-yl)methyl]pyrimidin-2-amine (also known as 4-chloro-6-methyl-N-[(3-methyl-1,2-oxazol-5-yl)methyl]pyrimidin-2-amine), used as starting material, was prepared as follows: a) <strong>[70183-89-0](3-methylisoxazol-5-yl)methanamine hydrochloride</strong> (also known as (3-methyl-1,2-oxazol-5-yl)methanamine hydrochloride; 2.09 g, 14.0 mmol) was dissolved in diglyme (8 ml) and di-iso-propylethylamine (2.43 ml) added. After a few minutes 6-methyl-2-methylsulfanyl-3H-pyrimidin-4-one (2.0 g, 12.8 mmol) was added in a single portion and the solution was then heated at 160 C. for 3 hours. The orange solution was allowed to cool to room temperature and then dissolved in dichloromethane and purified directly by chromatography on silica eluting with a mixture of 2.5-20% methanol in dichloromethane. Fractions containing product were combined and evaporated to leave a solid which was triturated with diethyl ether to give 6-methyl-2-[(3-methylisoxazol-5-yl)methylamino]-3H-pyrimidin-4-one (0.914 g, 32% yield). 1H NMR (400 MHz, DMSO): 2.02 (s, 3H), 2.2 (s, 3H), 4.56 (s, 2H), 5.5 (s, 1H), 6.19 (s, 1H), 6.94 (bs, 1H), 10.8 (bs, 1H).
  • 13
  • [ 887242-55-9 ]
  • [ 70183-89-0 ]
  • 3-([(2-chloro-6-methylphenyl)amino]carbonyl}amino)-N-[(3-methylisoxazol-5-yl)methyl]-2-naphthamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In dimethyl sulfoxide; at 20℃; for 20.0h; 3-([(2-chloro-6-methylphenyl)amino]carbonyl}amino)-2-naphthoic acid (from Example 5a) (0.044 g, 125 umol) was dissolved in 0.25 ml_ DMSO and added to a mixture of <strong>[70183-89-0](3-methyl-isoxazol-5-yl)-methylamine HCI</strong> (0.020 g, 134 umol) and DIEA (diisopropylethylamine, 87 uL, 500 umol) dissolved in 0.25 mL DMSO. DIC (1 ,3- diisopropylcarbodiimide, 60 uL, 375 umol) was added and the reaction mixture shaken at room temperature for 20 hours. The reaction mixture was directly subjected to HPLC purification to provide the title compound as a white solid. Yield = 0.019 g (34%). ESMS [M+H]+m/z 449.2.
  • 14
  • [ 24424-99-5 ]
  • [ 70183-89-0 ]
  • [ 154016-57-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; for 72.4167h; l-<strong>[70183-89-0](3-methylisoxazol-5-yl)methanamine hydrochloride</strong> (770mg, 5.18 mmol, 1-6), i-tert- butyl dicarbonate (1.13 g, 5.18 mmol), and triethylamine (795 uL, 5.7 mmol) were stirred in DCM (15 mL) at O0C for 5 minutes, warmed to room temperature and stirred for 20 minutes more. The reaction was placed in the freezer for 72 hours. The reaction was diluted with EtOAc, washed with water, saturated sodium bicarbonate and brine. The combined organics were dried over Na2SO4 and concentrated in vacuo to give the titled compound (1-7). ESI+ MS: 213[MH]+.
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