Methyl iodide → 2-Amino-4-(3,5-diacetylphenyl)amino-1,6-dimethylpyrimidinium iodide

HRID 357493

Reaction equation

HRID 357493 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15](=[O:17])[CH3:16])[CH:12]=[C:11]([C:18](=[O:20])[CH3:19])[CH:10]=2)[CH:5]=[C:4]([CH3:21])[N:3]=1.[CH3:22][I:23]>C(#N)C.O1CCCC1>[I-:23].[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([C:18](=[O:20])[CH3:19])[CH:12]=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=2)[CH:5]=[C:4]([CH3:21])[N+:3]=1[CH3:22]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 133109Cni H1194

Product 1

HCID 98453522-Amino-4-(3,5-diacetylphenyl)amino-1,6-dimethylpyrimidinium iodide

Reagents, catalysts & solvents 1

HCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

Compound No. 2, FIG. 1A: A suspension of Compound No. 11 (2-amino-4-(3,5-diacetylphenyl)amino-6-methylpyrimidine) (0.284 g), was suspended in 1:1 acetonitrile-tetrahydrofuran was treated with methyl iodide (2 mL) and heated at 40°-45° C. under a reflux condenser for 18 hr. Cooling and filtration gave 0.35 g of 2-amino-4-(3,5-diacetylphenyl)amino-1,6-dimethylpyrimidinium iodide, mp 292° C. 2-Amino-4-(3,5-diacetylphenyl)imino-1,4-dihydro-1,6-dimethylpyrimidine. A suspension of 21 g (49.3 mmole) of 2- amino-4-(3,5-diacetylphenyl)amino-1,6-dimethylpyrimidinium iodide (compound No. 2, synthesized as described in section 6.1) in 1:1 methanol/water (750 mL) at 60° C. was treated with excess 2N NaOH with cooling to maintain about 60° C. An additional 200 mL of water was added and the mixture was cooled in ice and filtered to give 14.69 g 2-amino-4-(3,5-diacetylphenyl)imino-1,4-dihydro-1,6-dimethylpyrimidine as yellow crystals, mp 219-220°.

Workup

  1. addition2, FIG. 1A: A suspension of Compound No
  2. temperatureheated at 40°-45° C. under a reflux condenser for 18 hr
  3. temperatureCooling
  4. filtrationfiltration

Sources & evidence

ORD record
ord-ec58426d35b64ce591c730f0fd381893
Source dataset
uspto-grants-1998_11
Patent number
US05840893

Linked notes

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