Hydrochloric Acid → (3-{[5-(4-Hydroxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxy)acetic acid

HRID 2189097Notes

Reaction equation

HRID 2189097 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:20]([NH:22][C:23]4[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=4)[O:26][CH2:27][C:28]([OH:30])=[O:29])=[N:19][CH:18]=[N:17][C:16]=3[O:15][C:14]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:9][CH:8]=1.Cl>ClCCl>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:20]([NH:22][C:23]4[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=4)[O:26][CH2:27][C:28]([OH:30])=[O:29])=[N:19][CH:18]=[N:17][C:16]=3[O:15][C:14]=2[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 582800653-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid

Product 1

HCID 25095119(3-{[5-(4-Hydroxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxy)acetic acidYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add 109 mg (0.435 mmol) of boron tribromide at RT to a mixture of 170 mg (0.364 mmol) of 3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid and 4.5 ml of dichloromethane. Stir the mixture at RT overnight and then hydrolyse with 1N hydrochloric acid. After adding dichloromethane, filter off the insoluble solid and dry overnight under high vacuum. 128.6 mg of the target compound are obtained, which can be purified further by recrystallization from isopropanol.

Workup

  1. filtrationfilter off the insoluble solid
  2. customdry overnight under high vacuum

Sources & evidence

ORD record
ord-778915560faa4c5ab532ae4257a78c25
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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