Methylamine → HCID 21846324, compound

HRID 343862Notes

Reaction equation

HRID 343862 reaction equation
C[O:2][C:3](=O)[CH:4]([NH:6][C:7]1[N:12]=[C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([F:23])=[CH:15][CH:14]=2)[CH:10]=[C:9]([CH:24]([CH3:26])[CH3:25])[N:8]=1)[CH3:5].[CH3:28][NH2:29]>>[CH:24]([C:9]1[N:8]=[C:7]([NH:6][CH:4]([CH3:5])[C:3]([NH:29][CH3:28])=[O:2])[N:12]=[C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([F:23])=[CH:15][CH:14]=2)[CH:10]=1)([CH3:26])[CH3:25]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 54026963HCID 54026963, compound

Product 1

HCID 21846324HCID 21846324, compound

Procedure

2-[6-Isopropyl-4-(4-fluoronaphth-1-yl)pyrimidin-2-ylamino]-propionic acid methyl ester was dissolved in ethanolic methyl amine solution (33%) and sonicated in a Branson ultrasonic bath for 3 hours. The solution was evaporated to dryness and taken up in methanol. Sufficient water was added to cause crystallization. The impure reaction product was further purified by silica gel column chromatography, eluting with methylene chloride/methanol and recrystallized from methanol/water to give 2-[6-isopropyl-4-(4-fluoronaphth-1-yl)pyrimidin-2-ylamino]-N-methyl-propionamide, m.p. 141.1°-142.0° C.

Workup

  1. customsonicated in a Branson ultrasonic bath for 3 hours
  2. customThe solution was evaporated to dryness
  3. additionSufficient water was added
  4. customcrystallization
  5. customThe impure reaction product was further purified by silica gel column chromatography
  6. washeluting with methylene chloride/methanol
  7. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-d65f43395e2445fcbda7f530b7985520
Source dataset
uspto-grants-1999_01
Patent number
US05863924

Reaction notes

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