Pivaloyl chloride → N-(4-Oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide

HRID 417832Notes

Reaction equation

HRID 417832 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[CH3:12][C:13]([CH3:18])([CH3:17])[C:14](Cl)=[O:15]>N1C=CC=CC=1>[CH3:12][C:13]([CH3:18])([CH3:17])[C:14]([NH:1][C:2]1[NH:3][C:4](=[O:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1)=[O:15]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 1354087147-Deazaguanine

Product 1

HCID 135512721N-(4-Oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamideYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-amino-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (186 g, 1.23 mol) in pyridine (2 L) was treated with trimethylacetyl chloride (475 g, 3.94 mol, 485 mL, 3.2 eq) at 90° C. for 2 h, to give a mixture of N(2)-monoacylated and N(2), N(7)-bisacylated material. The solvent was evaporated and the residue was taken up in aqueous ammonia (37% NH3, 310 mL) and MeOH (2 L), and stirred at rt for 30 min, to selectively cleave the N(7)-pivaloyl group. The solid was collected by filtration, washed with water (500 mL×5), and dried on high vacuum to give the title compound as a solid (193 g). Concentration of the mother liquor provided additional solid material, which was collected, washed with water (50 mL×5), and dried (77 g). The combined yield was 93% (HPLC purity 98.6%). tR: 4.57 min. 1H-NMR (DMSO-d6) δ 12.00, (br. s, 1H), 7.40 (br. s, 1H), 6.96 (q, 1H), 6.40 (q, 1H), 1.24 (s, 9H).

Workup

  1. customto give
  2. additiona mixture of N(2)-monoacylated and N(2), N(7)-bisacylated material
  3. customThe solvent was evaporated
  4. filtrationThe solid was collected by filtration
  5. washwashed with water (500 mL×5)
  6. customdried on high vacuum

Sources & evidence

ORD record
ord-c856e3eaba2c4c3ebbd712e41692b5f5
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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