Lithium hydroxide, monohydrate → HCID 11632767, compound

HRID 1432169Notes

Reaction equation

HRID 1432169 reaction equation
[Cl:1][C:2]1[S:28][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=4)[C:21]([O:23]C)=[O:22])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.O[Li].O>CO.O>[Cl:1][C:2]1[S:28][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][CH:11]3[CH2:16][CH2:15][N:14]([CH2:17][C:18]4[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=4)[C:21]([OH:23])=[O:22])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11647366HCID 11647366, compound

Product 1

HCID 11632767HCID 11632767, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Methyl 3-((4-(6-chlorothieno[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl)methyl)benzoate (127 mg, 0.3 mmol) was heated in a 25% MeOH—H2O solution at 90° C. for 3 h in the presence of LiOH—H2O (12.7 mg, 0.3 mmol). The solvent was removed under reduced pressure; the residue was dissolved in MeOH and filtered. The filtrate was evaporated to collect product in 79% yield (97 mg). 1H NMR (400 MHz, CD3OD) δ 8.27 (s, 1H), 7.92 (s, 1H), 7.85 (d, 1H), 7.50 (s, 1H), 7.42 (d, 1H), 7.33 (t, 1H), 4.11 (m, 1H), 3.59 (s, 2H), 2.98 (d, 2H), 2.20 (t, 2H), 2.00 (d, 2H), 1.68 (m, 2H); MS (ESI) m/z: Calculated for C19H20ClN4O2S, 403.1; Observed: 403.2 (M++1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in MeOH
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customto collect product in 79% yield (97 mg)

Sources & evidence

ORD record
ord-06aea33258834f47998baf68a14c33c3
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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