Water → 2-[[2-Amino-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methyl-1,3-propanediol

HRID 731527

Reaction equation

HRID 731527 reaction equation
Cl[C:2]1[C:3]2[S:20][C:19]([NH2:21])=[N:18][C:4]=2[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=2[F:17])[N:7]=1.CCN(C(C)C)C(C)C.[NH2:31][C:32]([CH3:37])([CH3:36])[CH:33]([OH:35])O.[OH2:38]>CN1C(=O)CCC1>[NH2:21][C:19]1[S:20][C:3]2[C:2]([NH:31][C:32]([CH3:37])([CH2:33][OH:35])[CH2:36][OH:38])=[N:7][C:6]([S:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=3[F:17])=[N:5][C:4]=2[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 52441742-Amino-2-methylpropane-1,1-diol2×HCID 112216507-Chloro-5-[[(2,3-difluorophenyl)methyl]thio]-thiazolo[4,5-d]pyrimidin-2-amine

Product 1

HCID 226490352-[[2-Amino-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-2-methyl-1,3-propanediolYield 42%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

The product from step (d) (1.5 g) was suspended in NMP (10 ml), then Hunigs base (1.5 ml) and 2-Amino-2-methylpropanediol (1.37 g) added. Reaction mixture heated to 110° C. under N2 for 4 hrs. A further aliquot of 2-Amino-2-methylpropanediol (0.685 g) was added and mixture heated at 110° C. for 5 hrs. Mixture poured in to water (400 ml) and solid was collected by filtration. Purified by column chromatography (EtOAc: Methanol (95:5)) to give 0.756 g of product. 42% yield.

Workup

  1. customReaction mixture
  2. temperaturemixture heated at 110° C. for 5 hrs
  3. filtrationwas collected by filtration
  4. customPurified by column chromatography (EtOAc: Methanol (95:5))

Sources & evidence

ORD record
ord-5e06f1e3b0214ea78b27093ecf157865
Source dataset
uspto-grants-2009_09
Patent number
US07585867B2

Linked notes

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