Ammonium Chloride → HCID 59829479, compound

HRID 2262272Notes

Reaction equation

HRID 2262272 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[S:21][C:20]([C:22]([OH:24])=O)=[CH:19][C:9]=3[N:10]=[C:11](C3C=NC=CC=3)[N:12]=2)[CH2:3][CH2:2]1.ON1C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)O.C(N(CC)C(C)C)(C)C.[Cl-:59].[NH4+:60]>CN(C=O)C.CCOC(C)=O>[Cl:59][C:11]1[N:12]=[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[C:8]2[S:21][C:20]([C:22]([NH2:60])=[O:24])=[CH:19][C:9]=2[N:10]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 21864398Tetramethyluronium hexafluorophosphateHCID 59817876HCID 59817876, compound

Product 1

HCID 59829479HCID 59829479, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-morpholino-2-(pyridine-3-yl)thieno[3,2-d]pyrimidine-6-carboxylic acid (610 mg, 2.04 mmol), 1-hydroxy-7-azabenzotriazole (56 mg, 0.4 mmol), O-(7-azabenzotriazol-1-yl)-(N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU; 1.2 g, 3.1 mmol), and N,N-diisopropylethylamine (1.4 mL, 8.1 mmol) in DMF (3 mL) was added ammonium chloride (330 mg, 6.1 mmol). The reaction mixture was stirred overnight at room temperature. The mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine. The aqueous layer was extracted with EtOAc. The combined organics were washed with saturated NaHCO3 and brine then dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-20% MeOH in CH2Cl2) to afford 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carboxamide (490 mg, 81% yield).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organics were washed with saturated NaHCO3 and brine
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (0-20% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-69cdeecc603744038979eea63bb09574
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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