Lithium Hydroxide → HCID 178454023, compound

HRID 1672494Notes

Reaction equation

HRID 1672494 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]2[N:25]=[CH:24][C:23]3[C:18](=[CH:19][C:20]([C:26]([O:28]C)=[O:27])=[CH:21][CH:22]=3)[N:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>CO>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]2[N:25]=[CH:24][C:23]3[C:18](=[CH:19][C:20]([C:26]([OH:28])=[O:27])=[CH:21][CH:22]=3)[N:17]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178497295HCID 178497295, compound

Product 1

HCID 178454023HCID 178454023, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The methyl 2-({trans-4-[(tert-butoxycarbonyl)amino]cyclohexyl}amino)quinazoline-7-carboxylate (1.0 g, 4.0 mmol) was dissolved in MeOH (20 ml). To this solution LiOH (538.0 mg, 22.5 mmol) was added and then heated to 50° C. for 16 hours. Evaporation of the solvent and partition with EtAc/H2O, followed by separation of the organic layers and evaporation provided the crude product. Purification using a silica gel column with 40% EA in heptane to give 780.0 mg of the desired product (yield 81.3%). 1H NMR (400 MHz, DMSO-d6) ppm 1.23-1.36 (m, 4H), 1.38 (s, 9H), 1.82 (s, 2H), 1.93-2.05 (m, 2H), 3.18-3.27 (m, 1H), 3.77 (s, 1H), 6.76 (d, J=8.06 Hz, 1H), 7.27 (d, J=8.06 Hz, 1H), 7.63-7.71 (m, 1H), 7.71-7.78 (m, 1H), 7.93 (s, 1H), 9.10 (s, 1H). (APCI); 387.5 ([M+H]+).

Workup

  1. customEvaporation of the solvent
  2. custompartition with EtAc/H2O
  3. customfollowed by separation of the organic layers and evaporation
  4. customprovided the crude product
  5. customPurification

Sources & evidence

ORD record
ord-7b87dbf029654a07b55650ce10a1de53
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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