Acetic Acid → Methyl (6-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)carbamate

HRID 1842584Notes

Reaction equation

HRID 1842584 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[C:8]([O:10]CC)=O.[CH3:13][O:14][C:15]([NH:17][C:18](=[N:21]C(OC)=O)SC)=[O:16].CC(O)=O.C[O-].[Na+]>CO>[CH3:7][C:5]1[NH:4][C:3]2[C:8](=[O:10])[NH:21][C:18]([NH:17][C:15](=[O:16])[O:14][CH3:13])=[N:1][C:2]=2[CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 10942334Sodium MethoxideHCID 24754830Ethyl 3-amino-5-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 135797452Methyl (6-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)carbamateYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The pyrrole 6 (2.68 g, 16 mmol) was dissolved in MeOH (40 mL), and 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (3.74 g, 18 mmol) was added followed by AcOH (4.6 mL). The mixture was stirred at room temperature overnight and became a thick paste. To the reaction mixture NaOMe in MeOH (25%) 45 mL was added, and stirring was continued at room temperature for 2 h. The mixture was neutralized with AcOH and the solid collected by filtration and washed well with water. After drying, 7 (2.44 g, 69%) was obtained as an off-white powder: mp 234-236° C.; TLC Rf0.22 (MeOH/CHCl3, 1:5); 1H NMR (DMSO-d6) δ 2.28 (s, 3 H, CH3), 3.73 (s, 3 H, OCH3), 5.95 (s, 1 H), 10.90 (s, 1 H), 11.10 (s, 1 H), 11.76 (1 H). Anal. (C9H10N4O3.0.79C6H6.0.55C7H8O3S) C, H, N.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 2 h
  3. filtrationthe solid collected by filtration
  4. washwashed well with water
  5. customAfter drying

Sources & evidence

ORD record
ord-6df4b62763df4901b903d04805e28176
Source dataset
uspto-grants-2015_02
Patent number
US08946239B2

Reaction notes

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