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1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → N-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-4-(morpholinomethyl)thiazol-2-amine

HRID 1684954
Notes
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Reaction equation

HRID 1684954 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[O:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[N:20]=[C:21]([NH2:24])[S:22][CH:23]=2)[CH2:14][CH2:13]1.CC(C)([O-])C.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[Br:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:24][C:21]2[S:22][CH:23]=[C:19]([CH2:18][N:15]3[CH2:16][CH2:17][O:12][CH2:13][CH2:14]3)[N:20]=2)=[N:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 21253444-(Morpholin-4-ylmethyl)-1,3-thiazol-2-amineHCID 23676156Sodium t-butoxideHCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazine

Product 1

HCID 57541337N-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-4-(morpholinomethyl)thiazol-2-amine
Yield 27%

Reagents, catalysts & solvents 2

HCID 72499888Dibenzalacetone palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Intermediate 3 (5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine, 140 mg, 0.50 mmol), Intermediate 6 (4-(1-morpholinomethyl) thiazol-2-ylamine, 120 mg, 0.60 mmol), sodium tert-butoxide (68 mg, 0.71 mmol), palladium dibenzylidene acetone (19 mg, 0.02 mmol) and Xantphos (23 mg, 0.04 mmol) were suspended in toluene (4 mL). The mixture is degassed with nitrogen for 5 min and then stirred at 90° C. for 16 h. The solvent is evaporated in vacuo to leave a brown residue. The residue is purified by column chromatography, eluting with 2% methanolic ammonia (7 N) in dichloromethane to give the title compound as a yellow powder (53 mg, 27%). 1H NMR (400 MHz, d6-DMSO) δ 2.53 (s, 4H, CH2CH2), 3.51 (s, 2H, CH2), 3.61 (m, 4H, CH2CH2), 6.99 (s, 1H), 8.13 (s, 1H), 8.61 (s, 1H), 8.75 (s, 1H).

Workup

  1. customThe mixture is degassed with nitrogen for 5 min
  2. customThe solvent is evaporated in vacuo
  3. customto leave a brown residue
  4. customThe residue is purified by column chromatography
  5. washeluting with 2% methanolic ammonia (7 N) in dichloromethane

Sources & evidence

ORD record
ord-f85e440e0c1a4d139be12b587a351691
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148369B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes