Ammonium Hydroxide → HCID 178458658, compound

HRID 1641386Notes

Reaction equation

HRID 1641386 reaction equation
[Cl:1][C:2]1[C:3]([NH:19][C:20]2[CH:24]=[C:23]([O:25][CH:26]([CH3:28])[CH3:27])[NH:22][N:21]=2)=[N:4][C:5]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)[CH3:11])=[N:6][C:7]=1Cl.[OH-].[NH4+:30]>C(O)CCC>[Cl:1][C:2]1[C:3]([NH:19][C:20]2[CH:24]=[C:23]([O:25][CH:26]([CH3:28])[CH3:27])[NH:22][N:21]=2)=[N:4][C:5]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)[CH3:11])=[N:6][C:7]=1[NH2:30]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 178458657HCID 178458657, compound

Product 1

HCID 178458658HCID 178458658, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
165 °C

Procedure

(S)-5,6-Dichloro-N2-(1-(5-fluoropyridin-2-yl)ethyl)-N4-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (Example 30, 0.100 g, 0.469 mmol) was mixed with n-butanol (1.75 ml) and ammonium hydroxide (1.75 ml, 28.2 mmol) in an Argonaut Endeaver reactor. This was sealed and heated to 165° C. for 48 hours. The solvent was removed under reduced pressure and the resulted residue was purified by reverse phase Biotage chromatography to give the title compound as a brownish solid (0.045 g, 24%). 1H NMR (400 MHz) δ 11.92 (s, 1H), 9.03 (s, 1H), 8.49 (s, 1H), 7.66 (m, 1H), 7.52 (s, 1H), 7.46 (m, 1H), 6.32 (s, 2H), 5.38 (s, 1H), 5.05 (s, 1H), 4.65 (m, 1H), 1.43 (d, J=7.2 Hz, 3H), 1.26 (d, J=6.0 Hz, 6H). MS: Calcd.: 406. Found: [M+H]+ 407.

Workup

  1. customThis was sealed
  2. customThe solvent was removed under reduced pressure
  3. customthe resulted residue was purified by reverse phase Biotage chromatography

Sources & evidence

ORD record
ord-f323288401e44f14b23d030e96e9686e
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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