Ammonia → HCID 22636886, compound

HRID 2416343Notes

Reaction equation

[CH2:1]([O:3][C:4]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:12]([F:23])[CH:11]=2)=[C:8]([O:24]COC)[CH:7]=[C:6]([CH2:28][C:29]2[C:30]([NH2:36])=[N:31][C:32]([NH2:35])=[N:33][CH:34]=2)[CH:5]=1)[CH3:2].Cl.N>CO>[NH2:35][C:32]1[N:31]=[C:30]([NH2:36])[C:29]([CH2:28][C:6]2[CH:7]=[C:8]([OH:24])[C:9]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[C:12]([F:23])[CH:11]=3)=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)=[CH:34][N:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-(6-ethoxy-3′-fluoro-2-methoxymethoxy-4′-morpholin-4-ylmethyl-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine (120 mg; 0.24 mmol) in 20 ml methanol is heated to 50° C., 2.7 ml 4.5 M hydrochloric acid in methanol are then added and the mixture is stirred for 1 hour at this temperature. The pale yellow solution is cooled to 0° C., adjusted to pH 10 with 25% aqueous ammonia solution and concentrated to a volume of 2 ml. 20 ml water are added to the residue and the mixture is extracted three times with 50 ml methylene chloride each time. The combined organic phases are dried over magnesium sulphate and concentrated. 57 mg (52%) 4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-3′-fluoro-4′-morpholin-4-ylmethyl-biphenyl-2-ol are obtained as a colourless powder.

Workup

concentrationconcentrated to a volume of 2 ml
addition20 ml water are added to the residue
extractionthe mixture is extracted three times with 50 ml methylene chloride each time
dry with materialThe combined organic phases are dried over magnesium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-0a28787081bf47ceb741cfa8df0bf9d4
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821980B1

Reaction notes

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