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[ CAS No. 5638-78-8 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 5638-78-8
Chemical Structure| 5638-78-8
Structure of 5638-78-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5638-78-8 ]

CAS No. :5638-78-8 MDL No. :MFCD20037392
Formula : C5H12ClN3O Boiling Point : -
Linear Structure Formula :- InChI Key :DUXSXDMXKUUYHP-UHFFFAOYSA-N
M.W : 165.62 Pubchem ID :12427952
Synonyms :

Calculated chemistry of [ 5638-78-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.19
TPSA : 62.34 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) : -7.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.33
Log Po/w (WLOGP) : -0.37
Log Po/w (MLOGP) : -0.44
Log Po/w (SILICOS-IT) : -0.32
Consensus Log Po/w : -0.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.59
Solubility : 42.3 mg/ml ; 0.255 mol/l
Class : Very soluble
Log S (Ali) : -0.52
Solubility : 50.3 mg/ml ; 0.303 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.24
Solubility : 286.0 mg/ml ; 1.73 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.05

Safety of [ 5638-78-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5638-78-8 ]

* 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 [ 5638-78-8 ]

[ 5638-78-8 ] Synthesis Path-Downstream   1~94

  • 1
  • [ 5638-78-8 ]
  • [ 105-56-6 ]
  • [ 104637-63-0 ]
  • 2
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  • [ 109-77-3 ]
  • [ 122324-16-7 ]
  • 4
  • [ 5638-78-8 ]
  • [ 123-06-8 ]
  • [ 78318-43-1 ]
  • 5
  • [ 5638-78-8 ]
  • [ 5147-80-8 ]
  • [ 78318-45-3 ]
  • 7
  • [ 17823-58-4 ]
  • [ 5638-78-8 ]
  • [ 78318-46-4 ]
  • 8
  • [ 56547-83-2 ]
  • [ 5638-78-8 ]
  • 3,4-dihydro-2-(4-morpholino)-4-oxo-6-phenylethyl-5,6,7,8-tetrahydropyrido<4,3-d>pyrimidine [ No CAS ]
  • 9
  • [ 5638-78-8 ]
  • [ 17238-66-3 ]
  • 10
  • [ 5638-78-8 ]
  • [ 292638-85-8 ]
  • [ 100185-63-5 ]
  • [ 100185-67-9 ]
  • 11
  • [ 5638-78-8 ]
  • [ 3788-94-1 ]
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  • 12
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  • [ 94-05-3 ]
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  • 13
  • [ 5638-78-8 ]
  • [ 87-13-8 ]
  • [ 25693-41-8 ]
  • 14
  • [ 2964-33-2 ]
  • [ 5638-78-8 ]
  • 5-(4-Chloro-benzyl)-2-morpholin-4-yl-pyrimidine-4,6-diamine [ No CAS ]
  • 15
  • [ 5553-92-4 ]
  • [ 5638-78-8 ]
  • 5-(4-Methoxy-benzyl)-2-morpholin-4-yl-pyrimidine-4,6-diamine [ No CAS ]
  • 16
  • [ 33901-53-0 ]
  • [ 5638-78-8 ]
  • 5-(4-Dimethylamino-benzyl)-2-morpholin-4-yl-pyrimidine-4,6-diamine [ No CAS ]
  • 17
  • [ 5553-86-6 ]
  • [ 5638-78-8 ]
  • 5-(4-Methyl-benzyl)-2-morpholin-4-yl-pyrimidine-4,6-diamine [ No CAS ]
  • 18
  • [ 5638-78-8 ]
  • [ 163590-23-6 ]
  • 5-Benzo[1,3]dioxol-5-ylmethyl-2-morpholin-4-yl-pyrimidine-4,6-diamine [ No CAS ]
  • 19
  • [ 5638-78-8 ]
  • potassium salt of 2-formyl-1,3-cyclohexanedione [ No CAS ]
  • [ 21599-38-2 ]
  • 20
  • [ 5638-78-8 ]
  • potassium salt of 5,5-dimethyl-2-formyl-1,3-cyclohexanedione [ No CAS ]
  • 7,7-dimethyl-2-morpholin-4-yl-7,8-dihydro-6<i>H</i>-quinazolin-5-one [ No CAS ]
  • 21
  • [ 5638-78-8 ]
  • potassium salt of 5-phenyl-2-formyl-1,3-cyclohexanedione [ No CAS ]
  • 2-morpholin-4-yl-7-phenyl-7,8-dihydro-6<i>H</i>-quinazolin-5-one [ No CAS ]
  • 22
  • [ 5638-78-8 ]
  • [ 17422-74-1 ]
  • [ 61466-28-2 ]
  • 23
  • [ 20730-58-9 ]
  • [ 5638-78-8 ]
  • [ 329924-46-1 ]
  • 24
  • [ 41467-29-2 ]
  • [ 5638-78-8 ]
  • [ 832075-84-0 ]
  • 25
  • [ 18451-46-2 ]
  • [ 5638-78-8 ]
  • 4-[4-(4-methoxy-phenyl)-6-pyridin-4-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 26
  • [ 5638-78-8 ]
  • (E)-1-(pyridin-4-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one [ No CAS ]
  • 4-[4-pyridin-4-yl-6-(3,4,5-trimethoxy-phenyl)-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 27
  • [ 5638-78-8 ]
  • 1-pyridin-4-yl-3-thiophen-2-ylpropenone [ No CAS ]
  • 4-(4-pyridin-4-yl-6-thiophen-2-yl-pyrimidin-2-yl)-morpholine [ No CAS ]
  • 28
  • [ 5638-78-8 ]
  • [ 16212-33-2 ]
  • 4-(4-pyridin-4-yl-6-<i>p</i>-tolyl-pyrimidin-2-yl)-morpholine [ No CAS ]
  • 29
  • [ 5638-78-8 ]
  • (E)-3-(3-methoxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one [ No CAS ]
  • 4-[4-(3-methoxy-phenyl)-6-pyridin-4-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 30
  • [ 5638-78-8 ]
  • [ 16232-00-1 ]
  • 4-[4-(4-chloro-phenyl)-6-pyridin-4-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 31
  • [ 5638-78-8 ]
  • 3-[4-(methylsulfanyl)phenyl]-1-(pyridin-4-yl)prop-2-en-1-one [ No CAS ]
  • 4-[4-(4-methylsulfanyl-phenyl)-6-pyridin-4-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 32
  • [ 5638-78-8 ]
  • 3-(3,4-dimethylphenyl)-1-(pyridin-4-yl)prop-2-en-1-one [ No CAS ]
  • 4-[4-(3,4-dimethyl-phenyl)-6-pyridin-4-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 33
  • [ 5638-78-8 ]
  • [ 16232-06-7 ]
  • 4-[4-(3-nitro-phenyl)-6-pyridin-4-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 35
  • [ 5638-78-8 ]
  • 3-(2,5-dimethoxyphenyl)-1-pyridin-4-ylpropenone [ No CAS ]
  • 4-[4-(2,5-dimethoxy-phenyl)-6-pyridin-4-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 36
  • [ 5638-78-8 ]
  • 3-(2,3-dimethoxyphenyl)-1-pyridin-4-ylpropenone [ No CAS ]
  • 4-[4-(2,3-dimethoxy-phenyl)-6-pyridin-4-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 37
  • [ 5638-78-8 ]
  • (E)-3-(4-Methoxy-naphthalen-1-yl)-1-pyridin-4-yl-propenone [ No CAS ]
  • 4-[4-(4-methoxy-naphthalen-1-yl)-6-pyridin-4-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 38
  • [ 5638-78-8 ]
  • 1-(pyridin-4-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one [ No CAS ]
  • 4-[4-pyridin-4-yl-6-(2,4,5-trimethoxy-phenyl)-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 39
  • [ 5638-78-8 ]
  • 5-Chloro-4-[1-chloro-1-dimethylamino-meth-(Z)-ylidene]-1-phenyl-3,4-dihydro-2H-pyrrolium; chloride [ No CAS ]
  • dimethyl-(2-morpholin-4-yl-7-phenyl-6,7-dihydro-5<i>H</i>-pyrrolo[2,3-<i>d</i>]pyrimidin-4-yl)-amine [ No CAS ]
  • 40
  • [ 5638-78-8 ]
  • [ 53940-08-2 ]
  • 4-(4-phenyl-6-pyridin-4-yl-pyrimidin-2-yl)-morpholine [ No CAS ]
  • 41
  • [ 22883-27-8 ]
  • [ 5638-78-8 ]
  • 3-(2-morpholin-4-yl-6-phenyl-pyrimidin-4-yl)-1<i>H</i>-indole [ No CAS ]
  • 42
  • [ 38470-67-6 ]
  • [ 5638-78-8 ]
  • 3-(2-morpholin-4-yl-6-<i>p</i>-tolyl-pyrimidin-4-yl)-1<i>H</i>-indole [ No CAS ]
  • 43
  • [ 38470-69-8 ]
  • [ 5638-78-8 ]
  • 3-[6-(4-methoxy-phenyl)-2-morpholin-4-yl-pyrimidin-4-yl]-1<i>H</i>-indole [ No CAS ]
  • 44
  • [ 184963-74-4 ]
  • [ 5638-78-8 ]
  • 3-[6-(2,5-dimethoxy-phenyl)-2-morpholin-4-yl-pyrimidin-4-yl]-1<i>H</i>-indole [ No CAS ]
  • 45
  • [ 5638-78-8 ]
  • [ 38470-72-3 ]
  • 3-[6-(4-chloro-phenyl)-2-morpholin-4-yl-pyrimidin-4-yl]-1<i>H</i>-indole [ No CAS ]
  • 46
  • [ 5638-78-8 ]
  • (E)-1-(3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)prop-2-en-1-one [ No CAS ]
  • 3-[6-(3,4-dimethoxy-phenyl)-2-morpholin-4-yl-pyrimidin-4-yl]-1<i>H</i>-indole [ No CAS ]
  • 47
  • [ 1201-38-3 ]
  • [ 5638-78-8 ]
  • [ 123-08-0 ]
  • 4-[6-(2,5-dimethoxy-phenyl)-2-morpholin-4-yl-pyrimidin-4-yl]-phenol [ No CAS ]
  • 48
  • [ 5638-78-8 ]
  • [ 123-08-0 ]
  • [ 98-86-2 ]
  • 4-(2-morpholin-4-yl-6-phenyl-pyrimidin-4-yl)-phenol [ No CAS ]
  • 49
  • [ 5638-78-8 ]
  • [ 123-08-0 ]
  • [ 122-00-9 ]
  • 4-(2-morpholin-4-yl-6-<i>p</i>-tolyl-pyrimidin-4-yl)-phenol [ No CAS ]
  • 50
  • [ 5638-78-8 ]
  • [ 123-08-0 ]
  • [ 100-06-1 ]
  • 4-[6-(4-methoxy-phenyl)-2-morpholin-4-yl-pyrimidin-4-yl]-phenol [ No CAS ]
  • 51
  • [ 5638-78-8 ]
  • [ 123-08-0 ]
  • [ 1131-62-0 ]
  • 4-[6-(3,4-dimethoxy-phenyl)-2-morpholin-4-yl-pyrimidin-4-yl]-phenol [ No CAS ]
  • 52
  • [ 5638-78-8 ]
  • [ 832075-87-3 ]
  • 53
  • [ 5638-78-8 ]
  • <i>N</i>,<i>N</i>-dimethyl-<i>N</i>'-(2-morpholin-4-yl-6-thiophen-2-yl-pyrimidin-4-yl)-propane-1,3-diamine [ No CAS ]
  • 54
  • [ 5638-78-8 ]
  • 4-[4-(4-methyl-piperazin-1-yl)-6-thiophen-2-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 55
  • [ 5638-78-8 ]
  • (3-imidazol-1-yl-propyl)-(2-morpholin-4-yl-6-thiophen-2-yl-pyrimidin-4-yl)-amine [ No CAS ]
  • 56
  • [ 5638-78-8 ]
  • 4-[4-(4-phenyl-piperazin-1-yl)-6-thiophen-2-yl-pyrimidin-2-yl]-morpholine [ No CAS ]
  • 57
  • [ 5638-78-8 ]
  • (2-morpholin-4-yl-ethyl)-(2-morpholin-4-yl-6-thiophen-2-yl-pyrimidin-4-yl)-amine [ No CAS ]
  • 58
  • [ 5638-78-8 ]
  • [ 167403-77-2 ]
  • 59
  • [ 5638-78-8 ]
  • [ 167403-78-3 ]
  • 60
  • [ 5638-78-8 ]
  • [ 346671-60-1 ]
  • 61
  • [ 5638-78-8 ]
  • 3-morpholin-4-yl-10-pyrrolidin-1-yl-10<i>H</i>-9-oxa-2,4-diaza-phenanthrene [ No CAS ]
  • 62
  • [ 5638-78-8 ]
  • 3,10-di-morpholin-4-yl-10<i>H</i>-9-oxa-2,4-diaza-phenanthrene [ No CAS ]
  • 63
  • [ 5638-78-8 ]
  • 3-morpholin-4-yl-10-piperidin-1-yl-10<i>H</i>-9-oxa-2,4-diaza-phenanthrene [ No CAS ]
  • 64
  • [ 5638-78-8 ]
  • [ 100185-63-5 ]
  • 69
  • [ 5638-78-8 ]
  • 3-[4-(2-methoxy-phenyl)-piperazin-1-yl]-1-(4-methyl-2-morpholin-4-yl-pyrimidin-5-yl)-propan-1-one [ No CAS ]
  • 71
  • [ 1369393-77-0 ]
  • [ 5638-78-8 ]
  • [ 1055905-51-5 ]
YieldReaction ConditionsOperation in experiment
A dry round bottom flask is charged with dry ETOH, and Na (3 eq) is added. The reaction mixture is stirred till complete dissolution OF NA, then morpholino carboxamidine hydrochloride (1.2 eq) is added, followed by compound 33 (1 eq). The reaction mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure and water is added to the residue. The solid thus obtained is filtered, washed with water and dried, to afford crude 34 which is used in the next step without further purification.
  • 72
  • [ 404569-73-9 ]
  • [ 5638-78-8 ]
  • 4-(3,5-dichlorophenyl)-6-methyl-2-(morpholine-4-yl)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With sodium acetate; EXAMPLE 63 Synthesis of 4-(3,5-dichlorophenyl)-6-methyl-2-(morpholine-4-yl)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide: The title compound was obtained by using 100 mg (0.266 mmol) of 2-acetyl-3-(3,5-dichlorophenyl)-N-(3-phenylpropyl) acrylamide, 83.8 mg (0.399 mmol) of morpholino-formamidine-hydrochloride and 32.7 mg (0.399 mmol) of sodium acetate, in the same manner as that of Example 61. Yield: 59.2 mg (0.122 mmol) (46%) MS (ESI, m/z) 485 (M+H)+ 483 (M-H)- 1H-NMR (CDCl3): 1.70 (2H, quint), 2.44-2.49 (5H, m), 3.27 (2H, q), 3.76 (4H, br), 3.87 (4H, br), 5.44 (1H, br), 7.07 (2H, d), 7.15-7.29 (3H, m), 7.37 (1H, s), 7.63 (2H, s).
  • 73
  • [ 39514-19-7 ]
  • [ 5638-78-8 ]
  • [ 957438-14-1 ]
  • 74
  • [ 127915-15-5 ]
  • [ 5638-78-8 ]
  • [ 1007206-27-0 ]
YieldReaction ConditionsOperation in experiment
28% Step B 4-[4,6-Dichloro-5-(2-chloroethyl)-pyrimidin-2-yl]-morpholine [Show Image] To 1M sodium methoxide solution prepared from sodium metal (3.19 g, 139 mmol) and methanol (140 ml), 2-oxotetrahydrofuran-3-carboxylic acid methyl ester (13.3 g, 92 mmol) and <strong>[5638-78-8]morpholinoformamidine hydrochloride</strong> (15.3 g, 92 mmol) were added, followed by refluxing for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was dissolved in phosphorus oxychloride (90 ml), followed by stirring at 100C for 10 hours. The reaction mixture was concentrated under reduced pressure, and ice (ca. 100 g) was added to the residue, which was neutralized with 5M aqueous sodium hydroxide solution, followed by extraction twice with ethyl acetate. The organic layer was washed with brine, and dried over sodium sulfate. The drying agent was filtered off and concentrated, and the resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=20/0 to 10/1), to obtain the desired compound (yellow powder, 8.4 g, 28%). 1H-NMR (270 MHz, CDCl3) delta (ppm): 3.20 (2H, t, J=7.9Hz), 3.66 (2H, t, J=7.9Hz), 3.70-3.81 (8H, m). ESI (LC-MS positive mode) m/z 296 [(M+H)+].
  • 75
  • [ 110-91-8 ]
  • [ 14527-26-5 ]
  • [ 5638-78-8 ]
  • 76
  • [ 5638-78-8 ]
  • [ 105-53-3 ]
  • [ 24193-00-8 ]
YieldReaction ConditionsOperation in experiment
39% With sodium; In ethyl [2]alcohol; for 3h;Reflux; Following a reported procedure,20 S-methylisothiourea sulfate (93) (2.00 g, 10.6 mmol, 1.00 equiv.),water (5.26 mL, 2.02 M) and morpholine (1.28 mL, 14.9 mmol, 1.40 equiv.) were added to a flask fittedwith a reflux condenser. The mixture was slowly heated to reflux and the reflux was maintained for 5minutes. A 2.36 M hot solution of barium chloride in water (BaCl2, 3.60 mL, 8.50 mmol, 0.80 equiv.) wasadded, and the mixture was then heated for additional 30 minutes. After filtration, the solvent wasremoved by applying a stream of dry nitrogen over 72 hours. The residue was heated in hot ethanol (1.5mL) and acetone (11 mL) and allowed to cool down, the precipitate was collected after overnightstanding to give white solid 96 (0.773 g, 5.94 mmol, 44%) which was used in the next step without furtherpurification.
  • 77
  • [ 1421621-95-5 ]
  • [ 5638-78-8 ]
  • [ 1421621-96-6 ]
YieldReaction ConditionsOperation in experiment
Morpholinoformamidine hydrochloride (578 mg, 3.50 mmol) was added to the suspension of sodium methoxide (190 mg, 3.52 mmol) in 1,4-dioxane (6.3 ml). After stirring at room temperature, N-methyl-3- (2-oxo-tetrahydro-furan-3-carbonyl)-benzenesulfonamide (899 mg, 3.18 mmol) was added and refluxed for 2 h. After cooling to room temperature, the mixture was acidified with 5 M HCl aq. (1.06 ml) and concentrated under reduced pressure. The residue was used in the next reaction without further purification.
  • 78
  • [ 127915-15-5 ]
  • [ 5638-78-8 ]
  • [ 1178564-17-4 ]
YieldReaction ConditionsOperation in experiment
With sodium; In methanol; for 2h;Reflux; Na (3.19 g, 139 mmol) was dissolved in MeOH and <strong>[5638-78-8]morpholinoformamidine hydrochloride</strong> (15.3 g, 92.0 mmol) and 41 (13.3 g, 92.0 mmol) was added. After refluxing for 2 h, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was used in the next reaction without further purification.
With sodium; In methanol; for 2h;Reflux; To a solution of Na (3.19 g, 139 mmol) in MeOH (140 mL) was added <strong>[5638-78-8]morpholinoformamidine hydrochloride</strong> (15.3 g, 92.0 mmol) and 4 (13.3 g, 92.0 mmol). After refluxing for 2 h, the mixture was cooled to an ambient temperature and concentrated under reduced pressure, which afforded 5-(2-hydroxyethyl)-2-morpholin-4-yl-pyrimidine-4,6-diol as a crude product.
  • 79
  • [ 64273-40-1 ]
  • [ 5638-78-8 ]
  • C8H10N4O4 [ No CAS ]
  • 80
  • [ 5638-78-8 ]
  • 4-chloro-2-morpholino-6-phenylpyrimidine-5-carbonitrile [ No CAS ]
  • 81
  • [ 5638-78-8 ]
  • 2-(morpholin-4-yl)-4-phenyl-6-[4-(7-chloroquinolin-4-yl)aminobutyl]aminopyrimidine-5-carbonitrile [ No CAS ]
  • 82
  • [ 5638-78-8 ]
  • [ 100-52-7 ]
  • [ 105-56-6 ]
  • 2-(morpholin-4-yl)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate; In ethanol; at 80℃; for 5h; The solution of N-morpholinyl guanidine hydrochloride (1.6 g, 12.40 mmol, 1 equiv), benzaldehyde (1.88 ml, 18.60 mmol, 1.5 equiv), and ethyl cyanoacetate (1.98 ml, 18.60 mmol, 1.5 equiv) in ethanol (50 ml), K2CO3 (2.56 g, 18.60 mmol, 1.5 equiv) was heated at 80 C for 5 h. The reaction mixture was cooled and filtered to isolate product. The recrystallisation of isolated product from methanol provided white crystalline solid in 78% yield which melts at temperature >250 C (methanol). IR (KBr): numax 1436, 1526, 1630, 2197, 3348 cm-1. 1H NMR (500 MHz, DMSO-d6, 25 C): 3.59 (d, 4H, J 4.6 Hz, 2×CH2), 3.64 (d, 4H, J 4.6 Hz, 2×CH2), 7.42 (t, 3H, J 3.2 Hz, ArH), 7.76-7.79 (m, 2H, ArH). 13C NMR (125 MHz, DMSO-d6, 25 C): 44.2, 66.7, 84.0, 122.2, 128.3, 128.4, 128.6, 129.3, 129.6, 139.5, 162.8, 168.1 and 173.0. Anal. Calcd. for C15H14N4O2: C, 63.82; H, 4.96; N, 19.85. Found: C, 63.89; H, 4.95; N, 19.96. EIMS: m/z 282 (M+). UV/vis (DMSO): lambdamax (epsilon/L mol-1 cm-1) 328 nm (43600).
  • 83
  • [ 110-91-8 ]
  • S-methylisothiourea hemisulphate [ No CAS ]
  • [ 5638-78-8 ]
YieldReaction ConditionsOperation in experiment
86% S-Methylisothioureahemisulphate (77.0 mmol), water(19.0 ml.), and morpholine (4.5 ml, 51.0 mmol) weretaken in a flask fitted with a reflux condenser. The mixture was slowly heatedand brought to boiling and then refluxed for 5 minutes.[1]A hot solution of barium chloride (25.4 mmol) in water (12.5 ml) was added andthe reaction mixture was heated for additional 0.5 h. Evaporation of thefiltrate under reduced pressure furnished a gum, which was dissolved in amixture of hot ethanol (5.0 ml), and acetone (3.70 ml). The hydrochloride saltthat separated was recrystallized from a mixture of 2-ethoxyethanol and ethylacetate to isolate 9b as crystallinesolid. Yield:86%.m.p.130-132 omicronC.IR (KBr): numax 1667, 3336 cm-1.1H NMR (500 MHz, D2O, 25 omicronC):delta 3.48 (t, 4H, J 5.1 Hz, 2×CH2), 3.79 (t, 4H, J 5.1Hz, 2×CH2). 13C NMR (125 MHz, D2O, 25 omicronC):delta 45.3, 65.7 and 80.6. Anal. Calcd. for C5H12ClN3O: C, 36.25 ; H, 7.25 ; N, 25.37. Found : C, 36.12 ; H, 7.23 ; N, 25.18. HRMS: m/z130.2961 (M+-Cl).[1]K.J.M. Andrews, N. Anand, A.R. Todd, A.Topham, Experiments on the synthesis of purine nucleosides. Part XXVI.9-D-Glucopyranosidoisoguanine. J.Chem. Soc.(1949) 2490-2497.
44% Following a reported procedure,20 S-methylisothiourea sulfate (93) (2.00 g, 10.6 mmol, 1.00 equiv.),water (5.26 mL, 2.02 M) and morpholine (1.28 mL, 14.9 mmol, 1.40 equiv.) were added to a flask fittedwith a reflux condenser. The mixture was slowly heated to reflux and the reflux was maintained for 5minutes. A 2.36 M hot solution of barium chloride in water (BaCl2, 3.60 mL, 8.50 mmol, 0.80 equiv.) wasadded, and the mixture was then heated for additional 30 minutes. After filtration, the solvent wasremoved by applying a stream of dry nitrogen over 72 hours. The residue was heated in hot ethanol (1.5mL) and acetone (11 mL) and allowed to cool down, the precipitate was collected after overnightstanding to give white solid 96 (0.773 g, 5.94 mmol, 44%) which was used in the next step without furtherpurification.
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  • [ 5638-78-8 ]
YieldReaction ConditionsOperation in experiment
66% With hydrogenchloride; In water; at 80℃; for 12h;Sealed tube; Green chemistry; General procedure: To N-substituted 2-amino-4,6-dimethoxypyrimidine (0.25 mmol) was added 4Maqueous HCl (5.0 mmol, 20.0 eq., 1.250 mL) at 80 C in a sealed tube. The reactionwas left to stir until deemed complete by TLC analysis (8 - 16 h). The reaction wascooled to room temperature and then diluted with EtOAc (4 mL). The phases werethen separated and the aqueous phase was further washed with EtOAc (2 × 5 mL).The aqueous phase was then washed with CH2Cl2/MeOH (85:15, 5 mL). The aqueousphase containing the guanidine compound was then concentrated under reducedpressure. If further purification was required then the guanidine product was diluted inthe minimum amount of water and passed through a plug of reverse phase silica (C8)eluting with water to yield the title compound.
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  • [4-[4-(2-aminopyrimidin-5-yl)-2-morpholino-5,6-dihydropyrrolo[2,3-d]pyrimidin-7-yl]-2-pyridyl]-(4-methylpiperazin-1-yl)methanone [ No CAS ]
  • 86
  • [ 5638-78-8 ]
  • [5-[4-(2-aminopyrimidin-5-yl)-2-morpholino-5,6-dihydropyrrolo[2,3-d]pyrimidin-7-yl]-2-pyridyl]-(4-methylpiperazin-1-yl)methanone [ No CAS ]
  • 87
  • [ 5638-78-8 ]
  • [5-[4-(2-aminopyrimidin-5-yl)-2-morpholino-5,6-dihydropyrrolo[2,3-d]pyrimidin-7-yl]-3-pyridyl]-(4-methylpiperazin-1-yl)methanone [ No CAS ]
  • 88
  • [ 5638-78-8 ]
  • [ 1007206-27-0 ]
  • 89
  • [ 5638-78-8 ]
  • methyl 3-[4-[2-[bis[(4-methoxyphenyl)methyl]amino]pyrimidin-5-yl]-2-morpholino-5,6-dihydropyrrolo[2,3-d]pyrimidin-7-yl]benzoate [ No CAS ]
  • 90
  • [ 5638-78-8 ]
  • 3-[4-[2-[bis[(4-methoxyphenyl)methyl]amino]pyrimidin-5-yl]-2-morpholino-5,6-dihydropyrrolo[2,3-d]pyrimidin-7-yl]benzoic acid [ No CAS ]
  • 91
  • [ 5638-78-8 ]
  • [ 1007208-63-0 ]
  • 92
  • [ 5638-78-8 ]
  • 4-[4-[2-[bis[(4-methoxyphenyl)methyl]amino]pyrimidin-5-yl]-2-morpholino-5,6-dihydropyrrolo[2,3-d]pyrimidin-7-yl]-3-fluorobenzoic acid [ No CAS ]
  • 93
  • [ 5638-78-8 ]
  • [ 1007208-13-0 ]
  • 94
  • [ 5638-78-8 ]
  • 5-[7-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-2-morpholino-5,6-dihydropyrrolo[2,3-d]pyrimidin-4-yl]pyrimidin-2-amine [ No CAS ]
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