Dimethylformamide → HCID 88852845, compound

HRID 521600Notes

Reaction equation

HRID 521600 reaction equation
C(NCCCN1C(S[C:18]2[C:26]([C:27]3O[CH:29]=[CH:30][N:31]=3)=[CH:25]C3OCOC=3C=2)=NC2C1=NC=NC=2N)(C)C.CC(NCCC[N:40]1[C:49]([S:50][C:51]2[CH:56]=[C:55]3[O:57][CH2:58]O[C:54]3=[CH:53][C:52]=2I)=[N:48][C:42]2[C:43]([NH2:47])=[N:44][CH:45]=[N:46][C:41]1=2)C.[CH2:61]([Sn](CCCC)(CCCC)C1OC=CN=1)[CH2:62]CC.[Li+].[Cl-].[CH3:81]N(C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:61]([C:52]1[CH:53]=[CH:54][C:55]([O:57][CH3:58])=[CH:56][C:51]=1[S:50][C:49]1[N:40]([CH2:29][CH2:30][NH:31][CH2:27][C:26]([CH3:25])([CH3:18])[CH3:81])[C:41]2[C:42]([N:48]=1)=[C:43]([NH2:47])[N:44]=[CH:45][N:46]=2)#[CH:62]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 9549213ZelavespibHCID 154861832-(Tri-n-butylstannyl)oxazoleHCID 67115611HCID 67115611, compound

Product 1

HCID 88852845HCID 88852845, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

9-(3-(isopropylamino)propyl)-8-(6-(oxazol-2-yl)benzo[d][1,3]dioxol-5-ylthio)-9H-purin-6-amine [DZ4-20]. A mixture of PU-H71 (30 mg, 0.0585 mmol), 2-(tri-n-butylstannyl)oxazole (83.8 mg, 49 μl, 0.234 mmol), LiCl (5 mg, 0.117 mmol) and Pd(PPh3)4 (6.7 mg, 0.0058 mmol) in DMF (1 mL) was evacuated and back filled with nitrogen. This was repeated four times then the reaction mixture was heated under nitrogen at 90° C. for 18 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (hexane:CH2Cl2:EtOAC:MeOH—NH3 (7N), 2:2:1:0.5) to give 20.8 mg (78%) of DZ4-20. 1H NMR (500 MHz, CDCl3/MeOH-d4) δ 8.25 (s, 1H), 7.75 (s, 1H), 7.46 (s, 1H), 7.27 (s, 1H), 6.71 (s, 1H), 6.06 (s, 2H), 4.26 (t, J=6.9 Hz, 2H), 2.75 (septet, J=6.3 Hz, 1H), 2.53 (t, J=6.9 Hz, 2H), 1.98 (m, 2H), 1.06 (d, J=6.3 Hz, 6H); HRMS (ESI) m/z [M+H]+ calcd. for C21H24N7O3S, 454.1661; found. 454.1650; HPLC: method A Rt=5.77, method B Rt=5.28.

Workup

  1. customwas evacuated
  2. additionback filled with nitrogen
  3. customSolvent was removed under reduced pressure
  4. customthe resulting residue was purified by preparatory TLC (hexane:CH2Cl2:EtOAC:MeOH—NH3 (7N), 2:2:1:0.5)
  5. customto give 20.8 mg (78%) of DZ4-20

Sources & evidence

ORD record
ord-8eaf03d20f7d4de582b131576728d3e0
Source dataset
uspto-grants-2016_05
Patent number
US09328114B2

Reaction notes

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