Acetic Acid → HCID 178441728, compound

HRID 1110058Notes

Reaction equation

HRID 1110058 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]([C:12]([O:14]C)=[O:13])[C:6]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[NH:33][N:32]=[N:31][N:30]=2)=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].CC(O)=O>CO>[CH2:1]([C:5]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]([C:12]([OH:14])=[O:13])[C:6]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[NH:33][N:32]=[N:31][N:30]=2)=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 178441729HCID 178441729, compound

Product 1

HCID 178441728HCID 178441728, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 68 4 mg (0.155 manol) 6-butyl-4-methoxycarbonyl-2-methyl-5-[(2'-(tetrazol-5-yl)biphen-4-yl)methyl]pyrimidine in 5 mL methanol was added ~0.300 mL 10% NaOH. After stirring at room temperature for 2.5 hours, the mixture was acidified with ~0.500 mL HOAc. Volatiles were removed in vacuo. The crude material was redissolved in methanol along with a couple of drops of TFA, then was HPLC'd using the following conditions: Rainin Dynamax® C-18 column, 25×2.14 cm w/Guard Column; gradient of acetonitrile in water 5 to 100% over 40 minutes at 5 mL/minute; gradient held at 82% for 7 minutes. A yield of 66.1 mg (100%) of the title compound was obtained. Rf 0.14 in 1/30/69 NH4OH/MeOH/CH2Cl2, visualized by UV; 1H-NMR (300 MHZ, CDCl3): δ~9.7-8.8 (v br s 2H) 7.97 (m, 1H), 7.52 (m, 2H), 7.37 (m, 1H), 7.00 (br s, 4H), 4.51 (br s, 2H), 2.86 (3 line m, 2H), 2.75 (br s, 3H), 1.62 (m, 2H), 1.36 (m, 2H), 0.88 (3 line m, 3H); MS(FAB) m/e 429 (M+1).

Workup

  1. customVolatiles were removed in vacuo
  2. dissolutionThe crude material was redissolved in methanol along with a couple of drops of TFA
  3. waitgradient of acetonitrile in water 5 to 100% over 40 minutes at 5 mL/minute
  4. waitgradient held at 82% for 7 minutes

Sources & evidence

ORD record
ord-d73fc30ebb6546129a58826205dd6568
Source dataset
uspto-grants-1994_06
Patent number
US05324729

Reaction notes

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