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Sodium Carbonate → 2-(1H-Indazol-4-yl)-6-(3-(methylsulfonyl)phenyl)-4-morpholinofuro[3,2-d]pyrimidine

HRID 2262042
Notes
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Reaction equation

HRID 2262042 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[O:10][C:9](I)=[CH:8][C:6]=2[N:7]=1.[CH3:18][S:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:21])=[O:20].C([O-])([O-])=O.[Na+].[Na+].CC1(C)C(C)(C)OB([C:45]2[CH:53]=[CH:52][CH:51]=[C:50]3[C:46]=2[CH:47]=[N:48][NH:49]3)O1>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:49]1[C:50]2[C:46](=[C:45]([C:2]3[N:3]=[C:4]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)[C:5]4[O:10][C:9]([C:26]5[CH:25]=[CH:24][CH:23]=[C:22]([S:19]([CH3:18])(=[O:21])=[O:20])[CH:27]=5)=[CH:8][C:6]=4[N:7]=3)[CH:53]=[CH:52][CH:51]=2)[CH:47]=[N:48]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium Carbonate2×HCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 595930702-Chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine

Product 1

HCID 595928562-(1H-Indazol-4-yl)-6-(3-(methylsulfonyl)phenyl)-4-morpholinofuro[3,2-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine (40 mg, 1.0 eq) was dissolved in acetonitrile (0.4 ml) and treated with 3-(methylsulfonyl)phenylboronic acid (23 mg, 1.05 eq), PdCl2(PPh3)2 (7.7 mg, 0.10 eq) and 1M Na2CO3 (0.33 ml). The vial was sealed and heated with stirring in the microwave to 100° C. for 30 minutes. Reaction mixture was quenched with saturated aq. NaHCO3 and extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated. The residue was dissolved in acetonitrile (0.4 ml) and treated with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 (53 mg, 2.0 eq), PdCl2(PPh3)2 (7.7 mg, 0.10 eq) and 1M Na2CO3 (0.33 ml). The vial was sealed and heated with stirring in the microwave to 150° C. for 15 minutes. The crude reaction mixture was concentrated and purified by reverse phase HPLC to afford 2-(1H-indazol-4-yl)-6-(3-(methylsulfonyl)phenyl)-4-morpholinofuro[3,2-d]pyrimidine 111 MS (Q1) 476 (M)+.

Workup

  1. customThe vial was sealed
  2. temperatureheated
  3. customReaction mixture
  4. customwas quenched with saturated aq. NaHCO3
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in acetonitrile (0.4 ml)
  9. customThe vial was sealed
  10. temperatureheated
  11. stirringwith stirring in the microwave to 150° C. for 15 minutes
  12. customThe crude reaction mixture
  13. concentrationwas concentrated
  14. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-f9dd4d69b5974e8fb6795ed7a1cc818b
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07846929B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes