Sodium → HCID 178518201, compound

HRID 251885Notes

Reaction equation

HRID 251885 reaction equation
C[O:2][C:3](=O)[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)[C:5](OC)=[O:6].[Na].Cl.[CH:19]([NH2:21])=[NH:20]>CO>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]2[C:5]([OH:6])=[N:20][CH:19]=[N:21][C:3]=2[OH:2])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 21750597Dimethyl (4-bromophenyl)propanedioate

Product 1

HCID 178518201HCID 178518201, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-(4-bromophenyl)-malonic acid dimethyl ester (11.73 g) in methanol (100 mL) is added at 0° C. to a solution of sodium (2.83 g) in methanol (100 mL). The mixture is stirred for 18 h at rt before formamidine hydrochloride (4.10 g) is added. The suspension is stirred at rt for 4 h. The solvent is removed and the residue is suspended in 10% aq. citric acid (100 mL) and stirred for 10 min. The white precipitate is collected, washed with 10% aq. citric acid, water, evaporated three times from CyHex and dried under high vacuum at 40° C. to give 5-(4-bromophenyl)-pyrimidine-4,6-diol (9.90 g) as a pale beige powder. LC-MS: tR=0.61 min, [M+H]+=267.07; 1H-NMR(D6-DMSO): 7.43-7.48 (m, 2H), 7.50-7.55 (m, 2H), 8.13 (s, 1H), 12.1 (s br, 2H).

Workup

  1. additionis added
  2. customThe solvent is removed
  3. stirringstirred for 10 min
  4. customThe white precipitate is collected
  5. washwashed with 10% aq. citric acid, water
  6. customevaporated three times from CyHex
  7. customdried under high vacuum at 40° C.

Sources & evidence

ORD record
ord-785c145cf0f344cdb1f3558503c16375
Source dataset
uspto-grants-2011_01
Patent number
US07868012B2

Reaction notes

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