Hydrochloric Acid → 4'-(2,4-Diamino-pyrimidin-5-ylmethyl)-2',6'-diethoxy-biphenyl-4-ol

HRID 2416299Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH2:10][C:11]2[C:12]([NH2:18])=[N:13][C:14]([NH2:17])=[N:15][CH:16]=2)[CH:7]=[C:6]([O:19][CH2:20][CH3:21])[C:5]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28]COC)=[CH:24][CH:23]=1)[CH3:2].Cl>CO>[NH2:17][C:14]1[N:13]=[C:12]([NH2:18])[C:11]([CH2:10][C:8]2[CH:7]=[C:6]([O:19][CH2:20][CH3:21])[C:5]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=2)=[CH:16][N:15]=1

Participants

Conditions

Temperature: 56 °C

Procedure

5-(2,6-Diethoxy-4′-methoxymethoxy-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine (10.06 g; 23.7 mmol) is dissolved in methanol (410 ml), and a 3 N hydrochloric acid solution in methanol (119.1 ml; 357.3 mmol) is added. The reaction mixture is stirred for 30 minutes at a temperature of 56° C. and concentrated. The grey residue is then stirred with water (400 ml), the pH is brought to 9 by addition of an aqueous saturated ammonia solution (approx. 8 ml) and the entire mixture is stirred for 15 minutes. The greyish suspension is filtered with suction and the residue is dried under a high vacuum. 8.85 g (98%) 4′-(2,4-diamino-pyrimidin-5-ylmethyl)-2′,6′-diethoxy-biphenyl-4-ol are obtained as a greyish powder.

Workup

concentrationconcentrated
stirringThe grey residue is then stirred with water (400 ml)
additionthe pH is brought to 9 by addition of an aqueous saturated ammonia solution (approx. 8 ml)
stirringthe entire mixture is stirred for 15 minutes
filtrationThe greyish suspension is filtered with suction
customthe residue is dried under a high vacuum

Sources & evidence

ORD record: ord-47b4b305b5cf44609bd95c9c63711389
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821980B1

Reaction notes

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