Sodium Hydroxide → (4-(6-Amino-5-(4-phenoxyphenyl)-pyrimidin-4-ylamino)-phenyl)-acetic acid

HRID 1522104Notes

Reaction equation

HRID 1522104 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)=[C:17]([NH2:32])[N:16]=[CH:15][N:14]=2)=[CH:8][CH:7]=1)C.O1CCOCC1.[OH-].[Na+]>>[NH2:32][C:17]1[N:16]=[CH:15][N:14]=[C:13]([NH:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:33])=[O:3])=[CH:7][CH:8]=2)[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 71092830(4-(6-Amino-5-(4-phenoxyphenyl)-pyrimidin-4-ylamino)-phenyl)-acetic acid ethyl ester

Product 1

HCID 71092854(4-(6-Amino-5-(4-phenoxyphenyl)-pyrimidin-4-ylamino)-phenyl)-acetic acidYield 87.3%

Procedure

To a vial with stirbar were added {4-[6-amino-5-(4-phenoxy-phenyl)-pyrimidin-4-ylamino]-phenyl}-acetic acid ethyl ester (1430.0 mg; 3.084 mmol; 1.0 eq.) dissolved in dioxane (15.0 ml; 176.040 mmol; 57.1 eq.), and aqueous sodium hydroxide (2 N, 9.3 ml; 18.504 mmol; 6.0 eq.). The reaction mixture was stirred at room temperature for 1.5 h. The reaction was quenched by the addition of water, and washed once with EtOAc. The aqueous phase was acidified with 1N hydrochloric acid. The precipitate was filtered and dried in vacuo to afford (4-(6-amino-5-(4-phenoxyphenyl)-pyrimidin-4-ylamino)-phenyl)-acetic acid (1.11 g, 85% yield) as white solid. The filtrate was extracted with EtOAc (2×). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to afford (4-(6-amino-5-(4-phenoxyphenyl)-pyrimidin-4-ylamino)-phenyl)-acetic acid (265 mg, 19% yield) as white solid. MS: m/z=413 [M+H]+. 1H-NMR (DMSO-d6) δ 12.20 (bs, 1H), 8.05 (s, 1H), 7.41-7-39 (m, 4H), 7.34-7.32 (d, 2H), 7.16-7.11 (m, 8H).

Workup

  1. customThe reaction was quenched by the addition of water
  2. washwashed once with EtOAc
  3. filtrationThe precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dae2eef49bc64d9c82714b0c1eb1c6a6
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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