Diisopropylethylamine → HCID 86613131, compound

HRID 60527

Reaction equation

HRID 60527 reaction equation
[CH2:1]([S:8][C:9]1[N:10]=[C:11](Cl)[C:12]2[S:17][C:16]([NH2:18])=[N:15][C:13]=2[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:29][NH:30][C@@H:31]([CH2:36][OH:37])[CH2:32][CH:33]([CH3:35])[CH3:34]>CN1C(=O)CCC1>[NH2:18][C:16]1[S:17][C:12]2[C:11]([N:30]([CH3:29])[C@H:31]([CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:36][OH:37])=[N:10][C:9]([S:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:14][C:13]=2[N:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 112782745-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amineHCID 59967423282525-49-9

Product 1

HCID 86613131HCID 86613131, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

5-(Benzylthio)-7-chloro[1,3]thiazolo[4,5-d]pyrimidin-2-amine (1.5 g, 4.86 mmol), DIPEA (691 mg, 5.35 mmol) and (R)—N-methylleucinol (956 mg, 7.29 mmol) were mixed in NMP (7.5 mL). The resulting solution was stirred at 110° C. under a nitrogen atmosphere for 2 days. After cooling to room temperature the reaction mixture was poured onto ice. The resulting yellow precipitate was collected by filtration, washed with water and dried in vacuo. The crude product was purified by flash column chromatography on silica (DCM:EtOAc 50:50 to 0:100) to give 1.42 g (72% yield) of the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. additionwas poured onto ice
  3. filtrationThe resulting yellow precipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customThe crude product was purified by flash column chromatography on silica (DCM:EtOAc 50:50 to 0:100)

Sources & evidence

ORD record
ord-f0a8b299aa924c8facecfbf85b09942e
Source dataset
uspto-grants-2016_09
Patent number
US09440992B2

Linked notes

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