Hydrochloric Acid → 5-[5-Chloro-2-(1-fluoro-1-methyl-ethyl)-methoxy-phenoxy]-pyrimidine-2,4-diamine

HRID 1677294Notes

Reaction equation

HRID 1677294 reaction equation
FC1C=C(OC)C=C[C:7]=1[O:8]C.CCN(S(F)(F)[F:18])CC.F[C:22]1[C:23](OC)=[CH:24][C:25]([CH:37]([CH3:39])[CH3:38])=[C:26]([CH:36]=1)[O:27][C:28]1[C:29]([NH2:35])=[N:30][C:31]([NH2:34])=[N:32][CH:33]=1.[ClH:42]>[Pd]>[Cl:42][C:22]1[CH:23]=[C:24]([O:8][CH3:7])[C:25]([C:37]([F:18])([CH3:38])[CH3:39])=[C:26]([CH:36]=1)[O:27][C:28]1[C:29]([NH2:35])=[N:30][C:31]([NH2:34])=[N:32][CH:33]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 123472(Diethylamino)sulfur trifluorideHCID 1450022-Fluoro-1,4-dimethoxybenzeneHCID 445736445-(5-Fluoro-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

Product 1

HCID 670534295-[5-Chloro-2-(1-fluoro-1-methyl-ethyl)-methoxy-phenoxy]-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Similarly prepared, but starting with 3-fluoro-1,4-dimethoxybenzene, and using hydrogenation with Pd/C in step 4 instead of DAST, was 5-(5-Fluro-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (0.778 g, 42%); mp (HCl salt)=239-241° C.; [MH]+=293.

Workup

  1. customSimilarly prepared

Sources & evidence

ORD record
ord-4c4640767b3240c5bfd4cf851f0a4e8f
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

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