Diisopropylethylamine → HCID 70981090, compound

HRID 2280749Notes

Reaction equation

HRID 2280749 reaction equation
[C:1]([NH:5][C:6]1[C:11]([C:12](O)=[O:13])=[CH:10][N:9]=[C:8]([S:15][CH3:16])[N:7]=1)([CH3:4])([CH3:3])[CH3:2].C[N:18](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.N.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]([NH:5][C:6]1[C:11]([C:12]([NH2:18])=[O:13])=[CH:10][N:9]=[C:8]([S:15][CH3:16])[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12820921Azane;hydrochlorideHCID 70981544HCID 70981544, compound

Product 1

HCID 70981090HCID 70981090, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(tert-Butylamino)-2-(methylthio)pyrimidine-5-carboxylic acid (2.83 g, 11.73 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluoro-phosphate(V) (6.69 g, 17.59 mmol) were combined in a 250 mL round-bottomed flask followed by the addition of DMF (29 mL). After that ammonia hydrochloride-(3.14 g, 58.6 mmol) and DIEA (10.21 mL, 58.6 mmol) were added and the mixture was stirred at room temperature overnight. The solvent was concentrated under reduced pressure and water (150 mL) was added. The resulting suspension was filtered, washed with water and dried under high vacuum overnight to afford 4-(tert-butylamino)-2-(methylthio)-pyrimidine-5-carboxamide (2.54 g, 10.57 mmol, 90% yield). MS (ESI) m/z 241.2

Workup

  1. concentrationThe solvent was concentrated under reduced pressure and water (150 mL)
  2. additionwas added
  3. filtrationThe resulting suspension was filtered
  4. washwashed with water
  5. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-b11d49de2b7b4836980c65505ecf2aee
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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