Dichloromethane → 4-methyl-N3-(3-pyrimidin-4-yl-pyridin-2-yl)-benzene-1,3-diamine

HRID 1361626Notes

Reaction equation

HRID 1361626 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH:15][C:16]2[C:21]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][N:23]=3)=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:9]=1)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>CCOC(C)=O>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([NH2:7])=[CH:9][C:10]=1[NH:15][C:16]1[C:21]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][N:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66970434[4-Methyl-3-(3-pyrimidin-4-yl-pyridin-2-ylamino)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 583962724-methyl-N3-(3-pyrimidin-4-yl-pyridin-2-yl)-benzene-1,3-diamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared according to the procedure described in J. Am. Chem. Soc. 1993, 115, 905-916. To [4-methyl-3-(3-pyrimidin-4-yl-pyridin-2-ylamino)-phenyl]-carbamic acid tert-butyl ester (550 mg, 1.46 mmol) was added CH2Cl2 (15 mL) and TFA (3.0 mL). The mixture was stirred for 3 h at 0° C., diluted with EtOAc and extracted with 50% aqueous Na2CO3. The organic layer was dried over Na2SO4, filtered and concentrated to yield 4-methyl-N3-(3-pyrimidin-4-yl-pyridin-2-yl)-benzene-1,3-diamine. MS m/z=278 [M+1]+. Calc'd for C16H15FN5: 277.33.

Workup

  1. customThe title compound was prepared
  2. extractionextracted with 50% aqueous Na2CO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4385e9ccf6024e37a97b688ef6dcffb9
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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