Ammonium Chloride → HCID 57818730, compound

HRID 705583Notes

Reaction equation

HRID 705583 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([O:9][CH2:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])[N:3]=1.[F:19][C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[CH2:22][N:23]=[C:24]=[O:25].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[NH4+].[Cl-]>CN(C=O)C>[C:14]([C:13]1[CH:12]=[C:11]([CH:18]=[CH:17][CH:16]=1)[CH2:10][O:9][C:4]1[N:3]=[C:2]([NH:1][C:24]([NH:23][CH2:22][C:21]2[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=2[F:19])=[O:25])[C:7]([F:8])=[CH:6][N:5]=1)#[N:15]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 6434981-Fluoro-2-(isocyanatomethyl)benzeneHCID 2733832Lithium HexamethyldisilazideHCID 57818679HCID 57818679, compound

Product 1

HCID 57818730HCID 57818730, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a magnetically stirred mixture of 3-(4-amino-5-fluoropyrimidin-2-yloxymethyl)-benzonitrile (0.075 g, 0.31 mmol) and 2-fluorobenzylisocyanate (0.59 mL, 0.46 mmol) in dry DMF (1.5 mL) was added LiHMDS (1.0 M in THF, 0.31 ml, 0.30 mmol). The vial was capped and the mixture stirred at room temperature for 8 h. Saturated aq. NH4Cl (3 ml) was added and the mixture was stirred for 4 h. The heterogeneous mixture was filtered, and the solid was washed with hot water, washed with E2O, and then dried under vacuum to give the title compound (0.075 g, 62%) as a white solid: mp 177-178° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.04 (s, 1H), 8.90 (t, J=5.7 Hz, 1H), 8.37 (d, J=2.8 Hz, 1H), 7.85 (br s, 1H), 7.80 (d, J=7.5 Hz, 1H), 7.74 (d, J=8.0 Hz, 1H), 7.60 (t, J=7.8 Hz, 1H), 7.42-7.38 (m, 1H), 7.35-7.29 (m, 1H), 7.20-7.14 (m, 2H), 5.33 (s, 2H), 4.49 (d, J=5.8 Hz, 2H); HPLC-MS (ESI) m/z 396.3 (M+H)+, 394.3 (M−H)−.

Workup

  1. customThe vial was capped
  2. stirringthe mixture was stirred for 4 h
  3. filtrationThe heterogeneous mixture was filtered
  4. washthe solid was washed with hot water
  5. washwashed with E2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a48f97f50b164587b777c00dfce18a51
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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