Hydrochloric Acid → 4-Amino-6-(4-aminophenyl)-2-(6-methylpyridin-2-ylmethylsulfanyl)-pyrimidine-5-carbonitrile

HRID 1668540Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=2)[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([NH:23]C(=O)C)=[CH:19][CH:18]=2)[C:3]=1[C:27]#[N:28].Cl>C(O)C.O>[NH2:1][C:2]1[C:3]([C:27]#[N:28])=[C:4]([C:17]2[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=2)[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=2)[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The compound (5.5 g) of Example 2 was suspended in a mixture of 50 mL of ethanol and 50 mL of water, and to the suspension was added 50 mL of 5N hydrochloric acid, and the resulting mixture was heated at 80° C. for 5 hours under stirring. After cooling the reaction mixture, the ethanol was removed under reduced pressure, and the residue was neutralized with 5N aqueous sodium hydroxide at ice temperature. The resulting crystal was filtrated, and recrystallized with ethanol to give 2.3 g of 4-amino-6-(4-aminophenyl)-2-(6-methylpyridin-2-ylmethylsulfanyl)-pyrimidine-5-carbonitrile as a light yellow powder.

Workup

temperatureAfter cooling the reaction mixture
customthe ethanol was removed under reduced pressure
filtrationThe resulting crystal was filtrated
customrecrystallized with ethanol

Sources & evidence

ORD record: ord-17ad7486afb44e2a8faa395d1ac2026d
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989446B2

Reaction notes

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