Ammonium Chloride → [6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl](4-hydroxy-4-methylpiperidin-1-yl)methanone

HRID 2171828Notes

Reaction equation

HRID 2171828 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:7][CH2:6][CH:5]([C:8]2[S:20][C:11]3[N:12]=[C:13]([CH3:19])[N:14]=[C:15]([C:16](O)=[O:17])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[CH3:22][C:23]1([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>CN1C(=O)CCC1>[CH3:21][C:2]1([CH3:1])[CH2:7][CH2:6][CH:5]([C:8]2[S:20][C:11]3[N:12]=[C:13]([CH3:19])[N:14]=[C:15]([C:16]([N:26]4[CH2:27][CH2:28][C:23]([OH:29])([CH3:22])[CH2:24][CH2:25]4)=[O:17])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 156491744-Methylpiperidin-4-olHCID 1180240036-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylic acid

Product 1

HCID 118024018[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl](4-hydroxy-4-methylpiperidin-1-yl)methanoneYield 60.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylic acid (150 mg), 4-methylpiperidin-4-ol (68 mg), HATU (262 mg), and NMP (2.1 mL) was added DIPEA (244 μL), followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous NH4Cl solution, followed by extraction with EtOAc. The organic layer was washed sequentially with water and brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column. The obtained purified product was suspended in IPE, collected by filtration, and then dried under reduced pressure to obtain [6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl](4-hydroxy-4-methylpiperidin-1-yl)methanone (120 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed sequentially with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column
  6. customThe obtained purified product
  7. filtrationcollected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-6ef8702c37c84a5185de9292017b81d2
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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