Hydrochloric Acid → HCID 19081731, compound

HRID 963441Notes

Reaction equation

HRID 963441 reaction equation
COC[O:4][C:5]1[C:6]([C:19]#[C:20][C:21]2[CH:22]=[C:23]([CH:33]=[C:34]([O:38][CH3:39])[C:35]=2[O:36][CH3:37])[CH2:24][C:25]2[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=2)=[CH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15]COC)[CH:11]=[CH:10][CH:9]=2.O.Cl>C1COCC1>[NH2:31][C:28]1[N:27]=[C:26]([NH2:32])[C:25]([CH2:24][C:23]2[CH:33]=[C:34]([O:38][CH3:39])[C:35]([O:36][CH3:37])=[C:21]([C:20]#[C:19][C:6]3[CH:7]=[C:8]4[C:13](=[CH:14][C:5]=3[OH:4])[C:12]([OH:15])=[CH:11][CH:10]=[CH:9]4)[CH:22]=2)=[CH:30][N:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19081531HCID 19081531, compound

Product 1

HCID 19081731HCID 19081731, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

146 mg of 5-[3-(3,5-bis-methoxymethoxy-naphthalen-2-ylethynyl)-4,5-dimethoxybenzyl]-pyrimidin-2,4-diamine (Example 12ap)) in 2.5 ml of THF, 2.5 ml of water and 2.5 ml of 6N hydrochloric acid are held at 50° for 7.5 hrs. The mixture is concentrated and the residue is chromatographed on silica gel with methylene chloride/methanol 9:1. 59 mg of 6-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-naphthalene-1,7-diol are isolated as a yellowish solid. Yield: 48%. Mass spectrum: peaks inter alia at 443 (M++H, 100%).

Workup

  1. customare held at 50° for 7.5 hrs
  2. concentrationThe mixture is concentrated
  3. customthe residue is chromatographed on silica gel with methylene chloride/methanol 9:1

Sources & evidence

ORD record
ord-875ff6b3333a44d6903359797ae53d38
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

Loading…