Stannous chloride dihydrate → HCID 178428296, compound

HRID 229330Notes

Reaction equation

HRID 229330 reaction equation
O.O.[Sn](Cl)Cl.[CH3:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[C:17](/[CH:19]=[CH:20]/[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:16]=[C:15]([NH:27][C:28]3[NH:32][N:31]=[C:30]([CH3:33])[CH:29]=3)[C:14]=2[N+:34]([O-])=O)[CH2:9][CH2:8]1>Cl.CO.C(OCC)(=O)C.[OH-].[Na+]>[CH3:6][N:7]1[CH2:8][CH2:9][N:10]([C:13]2[N:18]=[C:17](/[CH:19]=[CH:20]/[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:16]=[C:15]([NH:27][C:28]3[NH:32][N:31]=[C:30]([CH3:33])[CH:29]=3)[C:14]=2[NH2:34])[CH2:11][CH2:12]1

Participants

7

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 178428298HCID 178428298, compound

Product 1

HCID 178428296HCID 178428296, compoundYield 53.9%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of tin (II) chloride dihydrate (600 mg, 4.43 mmol) in concentrated hydrochloric acid (1 mL), 9.04 mmol) was cooled below 10° C. A solution of 6-(4-methylpiperazin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-5-nitro-2-[(E)-2-phenylvinyl]pyrimidin-4-amine (Example 4, 400 mg, 0.95 mmol) in methanol (20 mL) was added dropwise to the reaction mixture. The reaction was allowed to come to ambient temperature and was then heated to 60° C. for 3 hours. Progress of the reaction was monitored by TLC. The reaction mixture was reduced to ⅓rd volume of the original volume under vacuum. The residue was diluted with ethyl acetate (40 mL) and 1N NaOH (20 mL) was added to the reaction mixture. The organic layer was separated, dried and the solvent evaporated under reduced pressure. The residue was then triturated with ethyl acetate and hexane to afford 6-(4-methylpiperazin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-2-[(E)-2-phenylvinyl]pyrimidin-4,5-diamine as a yellow solid (200 mg). 1H NMR (400 MHz, DMSO-d6): δ 7.94 (br, 1H), 7.70 (d, 1H, J=16 Hz), 7.59 (m, 2H) 7.38 (m, 2H), 7.29 (m, 1H), 7.05 (d, 1H, J=16 Hz), 6.36 (br, 1H), 3.44 (br, 2H), 3.3 (br, 4H), 2.59 (br, 4H), 2.36 (s, 3H), 2.33 (s, 3H). MS (m/z) 391 (M+1).

Workup

  1. customto come to ambient temperature
  2. additionwas added to the reaction mixture
  3. customThe organic layer was separated
  4. customdried
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was then triturated with ethyl acetate and hexane

Sources & evidence

ORD record
ord-0f238a9d1f8040b8bf12f38b2b3b87c7
Source dataset
uspto-grants-2009_07
Patent number
US07563787B2

Reaction notes

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