2-Amino-4-chloro-6-methylpyrimidine → HCID 67199810, compound

HRID 547564Notes

Reaction equation

HRID 547564 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)=[O:3].[NH2:12][C:13]1[N:18]=[C:17]([Cl:19])[CH:16]=[C:15]([CH3:20])[N:14]=1>C(O)C.Cl>[ClH:19].[NH2:12][C:13]1[N:18]=[C:17]([NH:11][C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:2](=[O:3])[CH3:1])=[CH:6][CH:7]=2)[CH:16]=[C:15]([CH3:20])[N:14]=1

Participants

5

Reactant 2

HCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 312304-Aminoacetanilide

Product 1

HCID 67199810HCID 67199810, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of 4-aminoacetanilide 14 (3.55 g, 23.64 mmol) and 2-amino-4-chloro-6-methylpyrimidine 15 (3.73 g, 26 mmol) in ethanol (50 mL) was added. C.HCl (2 drops). The reaction mixture was stirred under reflux conditions for 2 h, cooled to 20° C. and the product was filtered washed with more ethanol and dried to give essentially pure 16 (6.38 g, 92%); mp (EtOH) 203-207° C.; 1H NMR [(CD3)2SO] δ 12.60 (br, 1 H, N+H), 10.50 (br 1 H, NH), 10.02 (s, 1 H, NH), 7.60-7.58 (br m, 6 H, NH2 & ArH), 6.13 (s, 1 H, H-5″), 2.26 (s, 3 H, CH3), 2.04 (s, 3 H, CH3); HRMS (FAB+), calc. for C13H16N5O (M+1) m/z 258.1355, found 258.1346.

Workup

  1. additionwas added
  2. filtrationthe product was filtered
  3. washwashed with more ethanol
  4. customdried

Sources & evidence

ORD record
ord-34f06b9ddf424cbfb208a189794c701b
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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