Phosphorus oxychloride → 7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

HRID 1072129

Reaction equation

HRID 1072129 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4](=O)[NH:3][CH:2]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:4]1[C:5]2[CH:9]=[CH:8][NH:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354086897-Deazahypoxanthine

Product 1

HCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-Yield 70%

Procedure

3,7-Dihydro-pyrrolo[2,3-d]pyrimidin-4-one (60 mg, 0.45 mmol) was reacted with 3.0 mL of phosphorus oxychloride to give 49 mg (70%) of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 12.57 (s, br, 1H, NH), 8.58 (s, 1H), 7.68 (dd, J=2.53, 3.36 Hz, 1H), and 6.59 (dd, J=1.86, 3.36 Hz, 1H). MS m/e 153 [M−1]+.

Sources & evidence

ORD record
ord-07386fddd3074c6cb2426bd0d4fd2e4d
Source dataset
uspto-grants-2005_06
Patent number
US06908930B2

Linked notes

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