2,4,5-Trichloropyrimidine → HCID 86633921, compound

HRID 1041071Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[C:21]2[CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][C:17](=[O:26])[NH:16][C:15]=2[CH:14]=[CH:13][C:12]=1[O:27][CH3:28]>>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[C:21]3[CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][C:17](=[O:26])[NH:16][C:15]=3[CH:14]=[CH:13][C:12]=2[O:27][CH3:28])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

Reactant 2

HCID 2372592,4,5-Trichloropyrimidine

HCID 67264619HCID 67264619, compound

Product 1

HCID 86633921HCID 86633921, compound

Conditions

Temperature: 120 °C

Procedure

A mixture of 2,4,5-Trichloro-pyrimidine (1.5 g, 0.0084 mol), 6-Amino-4-methanesulfonyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (0.400 g, 0.00140 mol) was heated at 120° C. for 48 hrs. The reaction was triturated with ethyl acetate and then with methanol giving 6-(2,5-Dichloro-pyrimidin-4-ylamino)-4-methanesulfonyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one the product as a gray solid (0.338 g, 51%). Mp 280-300d; LCMS (m/e) 432 (M); 1H-NMR (DMSO, 400 MHz) δ 10.23 (s, 1H), 9.34 (s, 1H), 8.34 (s, 1H), 7.20-7.17 (d, 1H, J=9.10 Hz), 7.14-7.11 (d, 1H, J=8.84 Hz),4.40-4.30 (m, 1H), 4.25-4.10 (m, 1H), 3.83 (s, 3H), 2.88 (s, 3H).

Workup

customThe reaction was triturated with ethyl acetate

Sources & evidence

ORD record: ord-4f44b92e615544a497b204bde5a892d7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

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