3-Chloro-4-fluoroaniline → HCID 57708337, compound

HRID 1668899Notes

Reaction equation

HRID 1668899 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[F:29])[NH2:25]>CCOC(C)=O>[Cl:21][C:22]1[CH:23]=[C:24]([NH:25][C:2]2[CH:3]=[C:4]([NH:8][CH:9]3[CH2:13][CH2:12][NH:11][CH2:10]3)[N:5]=[CH:6][N:7]=2)[CH:26]=[CH:27][C:28]=1[F:29]

Participants

4

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 22309469HCID 22309469, compound

Product 1

HCID 57708337HCID 57708337, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A neat mixture of tert-butyl 3-(6-chloropyrimidin-4-ylamino)pyrrolidin-1-carboxylate (354 mg, 1.18 mmol) and 3-chloro-4-fluoroaniline (3.03 g, 20.8 mmol) was heated at 140° C. for 21 hours. Upon cooling to ambient temperature, the melt was diluted with EtOAc and the mixture was stirred for 1 hour. A beige, amorphous precipitate was collected, washed with water and dried in vacuo at 50-60° C. giving 292 mg (80%) of N4-(3-chloro-4-fluorophenyl)-N6-(pyrrolidin-3-yl)pyrimidine-4,6-diamine. MS (APCI): (M+1)=308, (M−1)=306.

Workup

  1. temperatureUpon cooling to ambient temperature
  2. customA beige, amorphous precipitate was collected
  3. washwashed with water
  4. customdried in vacuo at 50-60° C.

Sources & evidence

ORD record
ord-3f4f0c076de14255b50b5a9632798776
Source dataset
uspto-grants-2011_08
Patent number
US07989465B2

Reaction notes

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