Dimethylformamide → N'-(6-Chloromethyl-pyrimidin-4-yl)-N,N-dimethyl-formamidine

HRID 1241403Notes

Reaction equation

HRID 1241403 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8]O)[CH:3]=1.[CH3:10][N:11]([CH:13]=O)[CH3:12].O=P(Cl)(Cl)[Cl:17].CCN(CC)CC>C(Cl)Cl>[Cl:17][CH2:8][C:4]1[N:5]=[CH:6][N:7]=[C:2]([N:1]=[CH:10][N:11]([CH3:13])[CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 21934615(6-Aminopyrimidin-4-yl)methanol

Product 1

HCID 21934611N'-(6-Chloromethyl-pyrimidin-4-yl)-N,N-dimethyl-formamidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (6-aminopyrimidin-4-yl)methanol (52 mg, 0.42 mmole) in CH2Cl2 (2 mL) was added DMF (0.03 mL, 0.42 mmole) then POCl3 (0.04 mL, 0.42 mmole) at room temperature. After 2 hours, Et3N (0.3 mL) was added and stirring continued. After 18 hours, the mixture was concentrated. The residue was taken up in saturated NaHCO3 and extracted with CH2Cl2 (4×). The combined organic layers were dried (MgSO4), filtered, and concentrated to give the title compound as its DMF amidine. 1H-NMR (300 MHz, d6-DMSO) δ 8.78 (s, 1H), 8.65 (s, 1H), 6.90 (s, 1H), 4.60 (s, 2H), 3.18 (s, 3H), 3.05 (s, 3H).

Workup

  1. customat room temperature
  2. waitAfter 18 hours
  3. concentrationthe mixture was concentrated
  4. extractionextracted with CH2Cl2 (4×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ce7021dd801b4d559bb1bce1bb683924
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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